Aberdeen offers small-town charm with easy access along Amtrak’s Northeast Corridor, making it a convenient stop for visitors exploring Harford County. Enjoy downtown dining, the weekly farmers market, year-round events at Festival Park, and nearby attractions like Ripken Stadium.    

Local favorites to explore in Aberdeen:    

• Festival Park​ (Adventure & Nature)

  Festival Park is Aberdeen's premier venue for outdoor concerts, festivals, and community celebrations throughout the year. Expansive green space and family-friendly amenities make it a popular gathering place for residents and visitors alike.    

• Aberdeen Historical Museum (Culture & History)

  The Aberdeen Historical Museum showcases artifacts, photographs, and exhibits that tell the story of the city's growth and military heritage. Visitors can learn about local history through displays highlighting the people and events that shaped the community.    

• Watchtower Brewing Company (Food & Drink)

  Small-batch craft beer is the focus at Watchtower Brewing Company, where a rotating tap list keeps locals coming back. The welcoming taproom frequently hosts trivia, live music, food trucks, and other community events.    

Annapolis pairs waterfront charm with rich history, offering visitors red-brick streets, 18th-century architecture, and iconic sites like the U.S. Naval Academy and Maryland State House. Explore City Dock, browse local shops and galleries, and enjoy dining, boating, and other Chesapeake Bay experiences.    

Local favorites to explore in Annapolis:    

• Schooner Woodwind Sailing Cruises (Adventure & Nature)

  Schooner Woodwind offers sailing cruises aboard authentic schooners on the Chesapeake Bay. Guests can enjoy scenic daytime, sunset, and specialty cruises while experiencing Annapolis from the water. The bar is stocked with wine and beer, including a nice selection of local craft beer. Sail on the boat that was used in the movie Wedding Crashers!    

• Seasons Olive Oil & Vinegar Taproom (Food & Drink)

  Discover hundreds of flavor combinations by sampling premium olive oils and aged balsamic vinegars before you buy. The shop also features gourmet foods, spices, and unique gifts for home cooks and food lovers.    

• Museum of Historic Annapolis (Culture & History)

  Four centuries of Annapolis history unfold through interactive exhibits and engaging storytelling. The museum provides an excellent introduction to the people, places, and events that shaped Maryland's capital city.    

Downtown Bel Air blends historic charm with a vibrant mix of locally owned shops, restaurants, and year-round community events. Stroll its tree-lined streets, enjoy a classic small-town atmosphere, and visit during signature events like the Maryland State BBQ Bash.    

Local favorites to explore in Bel Air:   

• Harford Artists Gallery (Culture & History)

  Discover original paintings, pottery, jewelry, photography, and more created by members of the Harford Artists' Association. Rotating exhibitions and special events make each visit a little different while showcasing the region's creative talent.    

• The Historical Society of Harford County (Culture & History)

  The Historical Society of Harford County plays a vital role in preserving and sharing the stories that define both downtown Bel Air and Harford County. Through its exhibits, educational programming, archival collections, and stewardship of local history, the organization creates meaningful cultural experiences that attract residents and visitors alike while strengthening community identity.    

• Independent Brewing Company (Food & Drink)

  Independent Brewing Company is a must-see destination for Bel Air’s experiential and flavorful tourism offerings, making it an ideal anchor stop within the Destination Main Street Adventure Trails. As a locally rooted craft brewery, it provides an authentic “taste of place” experience that connects visitors to the community through locally crafted beverages, rotating seasonal offerings, and a welcoming social atmosphere that encourages lingering and exploration.    

Nestled between Ocean City and Assateague Island, Berlin offers small-town charm in the heart of Worcester County. Its walkable downtown features local shops, dining, live entertainment, and easy access to outdoor adventures like kayaking, hiking, and bird watching.    

Local favorites to explore in Berlin:    

• The Mermaid Museum (Entertainment & Events)

  The Mermaid Museum provides a whimsical, family-friendly attraction that blends maritime folklore, interactive exhibits, and imaginative storytelling into a one-of-a-kind visitor experience. As one of Berlin’s most distinctive attractions, the museum reflects the town’s creative personality and artistic spirit while offering engaging exhibits suitable for all ages. The museum has become a recognizable tourism draw for Berlin and encourages visitors to explore the surrounding downtown district.    

• Baked Dessert Cafe (Food & Drink)

  Baked Dessert Café reflects Berlin’s creative culinary culture while celebrating the town’s agricultural and historical roots through its signature Peach Dumpling, recognized as the Town of Berlin’s official dessert. Inspired by Berlin’s history as a peach-growing community, the café connects local heritage with a memorable culinary experience that is unique to the destination.    

• Calvin B. Taylor House Museum (Culture & History)

  Learn how Berlin evolved from a crossroads village into one of Maryland's most celebrated small towns at the Calvin B. Taylor House Museum. Historic furnishings, artifacts, and changing exhibits bring Worcester County's past to life.    

Brunswick is a historic railroad town along the Potomac River, where Victorian character, scenic mountain views, and transportation heritage create a distinctive destination. Visitors can explore downtown shops and dining, visit the Brunswick Railroad Museum, and enjoy outdoor recreation along the river and C&O Canal towpath.    

Local favorites to explore in Brunswick:    

• Brunswick Heritage Museum (Culture & History)

  The Brunswick Heritage Museum is filled with engaging exhibits that celebrate the community’s history, from its railroad roots to its life along the C&O Canal. The museum features an entire floor dedicated to a large and lively model train layout, an impressive 1,700-square-foot HO scale display that train enthusiasts will especially appreciate. Admission is free, with a suggested donation of $5 per person or $20 per family.    

• B&O Railroad Park (Adventure & Nature)

  Make a fun stop at the new B & O Railroad Park, where Brunswick’s railroad spirit comes alive in a fresh and exciting way. Kids will love climbing the stairs of the historic WB Tower to the viewing platform to watch trains rumble through town, while adults take in sweeping views of the tracks and the Potomac. Follow the stamped railroad sidewalk to the standout feature of the park, the I‑beam swings that combine industrial railroad character with a fun, family‑friendly experience.    

• Maple & Rye Bakery (Food & Drink)

  Maple & Rye Bakery feels like the kind of place travelers hope to stumble upon by accident, and it’s easy to miss if you don’t know where to look. Set back from the street, just a few blocks from the C&O Canal and the Potomac River, it has quietly become one of western Maryland’s standout small-town food stops. Customer favorites include cinnamon rolls, savory croissants, scones, quiche and seasonal specials that change frequently.    

Set along the Choptank River, Cambridge offers a revitalized downtown with shops, galleries, restaurants, and waterfront charm on Maryland’s Eastern Shore. Visitors can enjoy local festivals, explore nearby Blackwater National Wildlife Refuge, and experience the city’s rich history through sites connected to Harriet Tubman and the Underground Railroad.    

Local favorites to explore in Cambridge:    

• Harriet Tubman Museum and Education Center (Culture & History)

  Gain a deeper understanding of Harriet Tubman's extraordinary life through exhibits that trace her journey to freedom. The museum also explores the history of the Underground Railroad and Tubman's enduring legacy on Maryland's Eastern Shore.    

• Harriet Tubman Beacon of Hope Statue​ (Culture & History)

  The Beacon of Hope statue in Cambridge, Maryland, is a 13-foot bronze sculpture by sculptor Wesley Wofford that honors Harriet Tubman's courage, resilience, and lifelong fight for freedom in the county where she was born. Depicting Tubman reaching down to lift her younger self, the monument symbolizes hope, liberation, and the power to overcome oppression.    

• Simmons Center Market (Shopping)

  Simmons Center Market is a multi-generational, family-owned and operated grocery store that has been a fixture in Downtown Cambridge for 89 years. They specialize in wholesale and retail grocery, fresh cut meats, seasonal flowers and made to order gift baskets for every occasion.    

• RAR Brewing (Food & Drink)

  Known for its inventive craft beers, RAR Brewing has become one of Maryland's premier brewery destinations. Pair a flight with creative pub fare while enjoying the lively taproom.    

Located in the heart of Queen Anne’s County, Centreville combines historic charm with specialty shops, unique dining, and a scenic setting near the Corsica River. Explore the town’s waterfront and historic landmarks, then visit nearby attractions like Tuckahoe State Park and the Museum of Eastern Shore Life.    

Local favorites to explore in Centreville:    

• Tucker House (Culture & History)

  Step back into Centreville's early history at the Tucker House, a restored 18th-century home that showcases life on Maryland's Eastern Shore. The museum features period furnishings, local artifacts, and exhibits that connect visitors to the community's past.    

• Uno Mas (Food & Drink)

  Bold flavors and fresh ingredients define Uno Mas, a downtown favorite serving Mexican-inspired dishes in a casual setting.    

• Queen Anne's County Centre for the Arts​ (Entertainment & Events)

  Art, education, and community come together at the Queen Anne's County Centre for the Arts. The venue hosts rotating exhibits, classes, performances, and cultural programs that showcase the creativity of local and regional artists.    

Set along the Chester River, Chestertown offers a classic Eastern Shore getaway with historic architecture, a vibrant arts scene, and a scenic waterfront. Explore galleries, shops, and dining downtown, then enjoy boating, biking, and views of the Schooner Sultana along the promenade.    

Local favorites to explore in Chestertown:    

• Park Row Floats (Adventure & Nature)

  Park Row Floats offers visitors an unexpected opportunity to relax, recharge, and experience wellness in a uniquely peaceful setting. The studio specializes in float therapy, a calming experience where guests rest effortlessly in warm, mineral-rich water inside a private float suite designed to reduce outside sound, light, and distractions. Many visitors describe float sessions as deeply restorative—helping to ease stress, quiet the mind, and create a rare sense of calm that’s hard to find in everyday life.    

• Modern Stone Age Kitchen (Food & Drink)

  Modern Stone Age Kitchen is a sourdough bakery and regenerative restaurant located in the heart of Chestertown, serving Maryland’s Eastern Shore with thoughtfully crafted food centered around sustainability, nutrition, and traditional preparation methods. Known for its naturally fermented sourdough breads, seasonal ingredients, and health-conscious menu, the restaurant has become a destination for visitors seeking fresh, flavorful meals crafted with quality and care.    

• Sultana Education Foundation (Culture & History)

  The Sultana Education Foundation offers visitors a signature Chesapeake Bay experience rooted in Chestertown’s rich maritime identity. Best known for the Sultana, a beautiful replica of a 1768 British merchant vessel, the organization connects people to the history, ecology, and culture of the Chesapeake.    

Cumberland is a historic Mountain Maryland destination where turn-of-the-century architecture, a vibrant arts scene, and a walkable downtown create a distinctive experience. Visitors can explore Canal Place and the downtown pedestrian mall, ride the Western Maryland Scenic Railroad, and access the C&O Canal Towpath and Great Allegheny Passage.    

Local favorites to explore in Cumberland:    

• Fore Axes (Entertainment & Events)

  The premier bar, axe-throwing, and golf experience lounge in Historic Downtown Cumberland. Continue the fun with corn hole, shuffle board, and Jenga! Special events include weekly trivia, line dancing lessons, DJ music, and more.    

• Allegany Museum (Culture & History)

  Featuring the crossroads of American history, the museum covers two accessible floors in a fully restored neo-classical revival building built in the 1930s. The Museum’s Mission is to engage the community by preserving and promoting the region’s unique heritage through artifacts, print and manuscript materials, maps, photographs, video, audio oral histories and paintings.    

• Queen City Scoop Shop (Food & Drink)

  Cool treats take center stage at Queen City Scoop Shop, where visitors can enjoy handcrafted ice cream, sundaes, and specialty desserts.    

Easton pairs Eastern Shore charm with a thriving arts and cultural scene, offering a historic downtown, distinctive shops, acclaimed dining, and access to Chesapeake Bay recreation. Visitors can explore galleries year-round and experience nationally recognized events like the Waterfowl Festival and Plein Air Easton.   

Local favorites to explore in Easton:    

• Hill Community Walking Tour (Cultural & Historical)

  Explore the history and heritage of Easton's Hill Community through a self-guided walking tour featuring important landmarks and stories. The tour highlights the neighborhood's African American history and the contributions of generations of residents.    

• Flying Cloud Poster Shop (Shopping)

  Flying Cloud Poster Shop provides an extensive collection of original vintage posters spanning a vast array of interests, from fashion, to food & beverage, travel, sports & automobiles, to war & propaganda.    

• Bas Rouge (Food & Drink)

  Bas Rouge is a contemporary European restaurant offering an impeccable integration of fine dining, a world-class wine list, and elegant service. The dining experience is refined, and the dishes are characterized by their polished adaptation of traditional Viennese and European classics, with ingredients from the finest local purveyors and farms. Head Chef Harley Peet was a 2024 James Beard Award Winner.    

• Out of the Fire (Food & Drink)

  Out of the Fire blends wood-fired cooking with global influences to create a menu that is both creative and approachable. Known for fresh ingredients and bold flavors, the restaurant has become a favorite among Easton diners.    

Elkton offers small-town charm and a unique history at the northern headwaters of the Chesapeake Bay, with a walkable downtown full of shops, restaurants, galleries, and community events. Known for its colorful past as the “Marriage Capital of the World,” Elkton is also a great stop for historic sites, nearby golf, and a relaxed weekend visit.    

Local favorites to explore in Elkton:    

• Elkton Music Hall (Entertainment & Events)

  The Elkton Music Hall offers visitors a unique opportunity to experience the heart of downtown Elkton through live entertainment, local culture, and community connection. Guests can enjoy live music and special events while also exploring nearby restaurants, shops, and attractions within walking distance.    

• Elk River Brewing (Food & Drink)

  Elk River Brewing Co. offers visitors a welcoming and authentic taste of Cecil County’s growing craft beverage scene. The brewery frequently hosts live entertainment, community events, and social gatherings that create a vibrant local atmosphere for both residents and visitors.    

• Cecil College Elkton Station Gallery (Culture & History)

  The Elkton Station Gallery provides a space for artists to share their work through rotating exhibitions and special showcases. Located in a historic setting, the gallery highlights creativity from Cecil County and beyond.    

Ellicott City’s historic Main Street blends early American charm with more than 200 18th- and 19th-century buildings, making it one of Maryland’s most distinctive downtown destinations. Visitors can explore unique shops, galleries, and restaurants, discover the town’s railroad history, and enjoy popular events like First Fridays and Main Street Music Fest.    

Local favorites to explore in Ellicott City:    

• B&O Museum Ellicott City (Culture & History)

  Visit one of America's oldest surviving railroad stations and discover Ellicott City's role in the nation's transportation history. The museum features a miniaturization of the original route of the railroad between Baltimore and Ellicott City.    

• Manor Hill Tavern (Food & Drink)

  Manor Hill Tavern occupies the historic Taylor’s Row in Old Ellicott City. Built in the mid-19th Century, this iconic series of buildings initially served the livery trade of the area. Local artwork hangs throughout the Tavern’s many rooms and a newly commissioned mural adorns a main wall, a nod to the eclectic and vibrant artistic community of Old Ellicott City.    

• MD History Tours Ellicott City (Culture & History)

  Step back in time with Ellicott City History Tours, where visitors can explore one of Maryland’s oldest and most storied communities. Guided by knowledgeable locals, these walking tours highlight the rich heritage, historic architecture, and pivotal moments that shaped Old Ellicott City.    

Downtown Frederick is a vibrant arts, dining, and shopping destination where more than 200 specialty shops, galleries, and restaurants fill a beautifully revitalized historic district. Visitors can explore 50 blocks of rich architecture and American history, enjoy guided tours and signature events, and experience one of Maryland’s most dynamic downtowns.    

Local favorites to explore in Frederick:    

• Surelocked In Escape Games (Entertainment & Events)

  Put your teamwork and problem-solving skills to the test at Surelocked In Escape Games, where immersive rooms challenge groups to uncover clues and complete themed missions. Each team has 60 minutes to crack the code, solve the riddles, and escape! Family-friendly and fun for all ages.    

• National Museum of Civil War Medicine (Culture & History)

  Explore the evolution of medical care during one of America's most defining conflicts at the National Museum of Civil War Medicine. Through artifacts, exhibits, and personal stories, the museum reveals how Civil War medicine shaped the future of healthcare.    

• Backslash Burger (Food & Drink)

  Creative burgers, hand-cut fries, and inventive toppings are the focus at Backslash Burger in downtown Frederick. Burgers are made of half beef/half bacon "smash burger" which is the foundation. From there, everything they do is intentional. A favorite among locals and visitors.    

Frostburg blends Appalachian character with a vibrant arts and entertainment scene, making it a standout destination in Mountain Maryland. Visitors can enjoy live performances through Frostburg State University’s Cultural Events Series, explore local dining and downtown charm, and stop along the Western Maryland Scenic Railroad route.    

Local favorites to explore in Frostburg:    

• Tracks and Yaks (Adventure & Nature)

  As one of the few rail-bike excursions in the country, Tracks & Yaks provides a unique outdoor experience for all ages, fitness levels, and abilities. Gliding downhill along the historic Western Maryland Scenic Railroad, visitors are surrounded by the stunning scenery of the Allegheny Mountains, immersed in history, and are treated to an adventure that can only be found in Frostburg, MD.    

• Mountain City Traditional Arts (Shopping)

  Mountain City Traditional Arts is dedicated to the education, sales, documentation, and perpetuation of regional art and cultural heritage. The venue features a diverse display of local artwork, hand-crafted items, and Appalachian-based products, and regularly hosts live music, literary readings, and international performances as part of the World Artist Experiences program.    

• Princess Restaurant​ (Food & Drink)

  Princess Restaurant has been serving up delicious food in downtown Frostburg for over 80 years. Diners can experience the original booths, tableside jukeboxes, and diner counter for a fun, retro vibe. One of Allegany County's most beloved restaurants, the Princess is known for their creative milkshakes, belt-busting breakfasts, and classic diner menu.    

Hagerstown, known as “Hub City,” offers a lively mix of history, arts, dining, and downtown energy in the heart of Western Maryland. Explore specialty shops and diverse restaurants, enjoy performances and exhibits in Maryland’s first Arts & Entertainment District, and take in year-round events, parks, and nearby trails.    

Local favorites to explore in Hagerstown:    

• Meritus Park (Entertainment & Events)

  Home to the Hagerstown Flying Boxcars, Meritus Park brings professional sports, public art, entertainment, dining, and walkable downtown experiences into one destination. The stadium attracts thousands of visitors throughout the tourism season while also serving as a hub for festivals, community events, concerts, and cultural programming connected to the Arts & Entertainment District.    

• Maryland Theatre (Entertainment & Events)

  Since 1915, the Maryland Theatre has been a centerpiece of Hagerstown's arts and entertainment scene. The historic theater hosts a wide range of performances and programming including concerts, theatrical productions, symphony performances, dance recitals, film screenings, educational programs, and community events that attract both residents and regional visitors throughout the year.    

• Sofrito's Puerto Rican Cuisine​ (Food & Drink)

  Sofrito's Puerto Rican Cuisine brings authentic island flavors to downtown Hagerstown with traditional dishes inspired by Puerto Rico's culinary heritage. The restaurant contributes to the city’s growing reputation as a diverse culinary destination through traditional dishes, vibrant flavors, and cultural authenticity that provide visitors with a memorable dining experience not commonly found elsewhere in the region.    

Set where the Susquehanna meets the Chesapeake Bay, Havre de Grace blends waterfront beauty, historic character, and a lively downtown filled with shops, galleries, and dining. Stroll the boardwalk, visit landmarks like Concord Point Lighthouse and the Decoy Museum, or enjoy boating, birding, and other outdoor recreation by the water.    

Local favorites to explore in Havre de Grace:    

• Washington Street Books & Music (Shopping)

  Washington Street Books & Music is known for its massive assortment of books, music, comics, and toys. Be sure to check out the Entertainment Museum, featuring a stunning display of over 50 original movie costumes and props, including the world's largest collection of costumes from The Hunger Games franchise.    

• Bella's Tea Room (Food & Drink)

  Growing up in Peru, afternoon tea was a cherished daily ritual for the owner of Bella’s Tea Room, a beautiful tradition she was determined to bring to the heart of Havre de Grace. Today, the tea room offers a quintessential high tea experience, featuring delicate petite sandwiches, freshly baked scones, and exquisite sweets.    

• The Luckiest Light (Culture & History)

  Nestled in the heart of downtown Havre de Grace, The Luckiest Light is a vibrant, inclusive creative space where artists of all abilities are celebrated side by side. Founded with a mission to shine a light on artists who are often overlooked, the gallery has quickly become a beacon for emerging, established, disabled, and community artists throughout the region.    

Leonardtown offers small-town charm in a scenic Southern Maryland setting, with a historic downtown, welcoming town square, and a vibrant arts and culture scene. Stroll local shops and galleries, enjoy acclaimed dining, and plan your visit around the concerts, festivals, and community events that bring downtown to life.    

Local favorites to explore in Leonardtown:    

• Butterfly Trail (Adventure & Nature)

  This family-friendly trail highlights historic landmarks, beautiful outdoor spaces, hidden works of art, local businesses, and fun discoveries throughout Leonardtown. Along the way, visitors can enjoy the Butterfly Trail Adventure, search for trail markers, explore public art, and learn more about the places that make Leonardtown special.    

• Old Jail Museum (Culture & History)

  Built in 1876 and in use until 1945 by the oldest sheriff’s office in the nation, this granite block and brick structure retains its original upstairs cells where prisoners were once segregated by gender and race. The jail keeper's quarters downstairs house-related artifacts. The site also features the Leonardtown Visitor Center and a museum store.    

• The Front Porch (Food & Drink)

  Set inside the historic Sterling House, The Front Porch offers creative Southern Coastal cuisine in a cozy, casual space. Warm décor, original hardwood floors, and local photography create a relaxed feel for locals and visitors alike. The friendly team delivers gracious service, while the menu features starters, soups, salads, sandwiches, and entrées with daily specials and seasonal ingredients.    

Long Branch offers a vibrant, family-friendly downtown experience in Montgomery County, with locally owned restaurants and shops, colorful public art, and a strong sense of community. Located between downtown Silver Spring and Takoma Park, it also hosts lively events and will soon be even more connected with a future Purple Line station.    

Local favorites to explore in Long Branch:    

• El Golfo (Food & Drink)

  El Golfo has been a Long Branch favorite for decades, serving a mix of Mexican and Central American-inspired dishes in a colorful, family-friendly setting. The restaurant reflects the neighborhood's diverse culture and vibrant community.    

• Mural Tour (Adventure & Nature)

  Explore Long Branch through a collection of vibrant murals that celebrate the neighborhood's diversity, history, and creativity. The self-guided experience turns the streetscape into an outdoor gallery.    

• Ocean City Seafood (Food & Drink)

  Ocean City Seafood offers a fresh fish market, with daily shipments of fresh Rockfish, Oysters, and Long Neck Clams among many other fish and sea fare from Maryland’s Eastern Shore.    

Surrounded by the scenic beauty of the Middletown Valley, Middletown offers small-town charm, local shops, dining, and a strong sense of community. Rich in American history, the town is especially worth visiting during the annual Middletown Heritage Festival, which celebrates its heritage with living history, family activities, and entertainment.    

Local favorites to explore in Middletown:    

• Middletown Welcome Center (Culture & History)

  Start your visit to Middletown at the Welcome Center, where guests can learn about local attractions, events, and the town's history. The center serves as a helpful resource for exploring the surrounding valley.    

• More Ice Cream (Food & Drink)

  More Ice Cream is a lovely historic home-turned-ice cream parlor, perfect for sitting, relaxing, and enjoying top-notch ice cream.    

• Aleko's Village Cafe (Food & Drink)

  Aleko's Village Cafe offers Greek food with locally-sourced ingredients and made-to-order dishes. Named Best Greek Restaurant in Frederick County by the Frederick News Post. A large outside porch faces towards Main Street and towards South Mountain, making outdoor dining a lovely experience.    

Mount Airy blends railroad history with classic small-town charm, offering a welcoming downtown filled with quaint historic buildings and community spirit. Visitors can explore its local history and plan a trip around popular events like Celebrate Mount Airy, Oktoberfest, and the town’s Old-Fashioned Main Street Christmas.    

Local favorites to explore in Mount Airy:    

• Mt. Airy Lanes (Entertainment & Events)

  Mount Airy Lanes stands out as one of the community’s most reliable, family‑friendly entertainment anchors, offering an experience that blends nostalgia, accessibility, and genuine small‑town charm. As a duckpin bowling alley, it provides an activity that is easy for children to learn, fun for teens, and still engaging for adults—making it a rare multigenerational attraction that families can enjoy together.    

• Rheb's Candies (Shopping)

  Handcrafted chocolates and nostalgic sweets have made Rheb's Candies a Maryland favorite for generations. Visitors can watch candy-making traditions continue while selecting from a wide variety of treats and gifts.    

• Mt. Airy Caboose Visitor Center (Culture & History)

  A restored railroad caboose serves as a unique gateway to Mount Airy's history and attractions.    

Oakland combines mountain-town charm with a lively historic downtown in the heart of Garrett County, just minutes from Deep Creek Lake. Stroll pedestrian-friendly shops, dining, arts and history attractions, then explore nearby outdoor gems like Swallow Falls and the region’s lakes, forests, and trails.    

Local favorites to explore in Oakland:    

• Garrett County Historical Society Museums (Culture & History)

  The Garrett County Historical Society Museums are an important cultural and historical asset for the community, preserving and sharing the heritage of Garrett County through exhibits, archives, and educational programming.    

• Englanders (Food & Drink)

  Englanders brings classic American dining to downtown Oakland. Known for its welcoming atmosphere and generous menu, the restaurant has long been a gathering place for locals and visitors exploring Garrett County.    

• Oakland B&O Museum (Culture & History)

  The Oakland B&O Museum preserves and shares the railroad history that helped shape the development of Garrett County and the Town of Oakland. Housed in the historic Baltimore & Ohio Railroad station, the museum offers exhibits, artifacts, and educational experiences that highlight the region’s transportation heritage and connection to Maryland’s rail history.    

Ocean City is Maryland’s only oceanfront destination, offering 10 miles of beaches, a classic boardwalk, and endless ways to enjoy the coast year-round. Visitors can enjoy shopping, dining, and lodging alongside fishing, boating, watersports, golf, and other bayside and beachfront recreation.    

Local favorites to explore in Ocean City:    

• Ocean City Boardwalk (Adventure & Nature)

  Stretching along the Atlantic shoreline, the Ocean City Boardwalk is one of Maryland's most recognizable attractions. Visitors can enjoy amusement rides, arcades, shops, restaurants, and classic seaside entertainment along this iconic destination.    

• Ocean City Life Saving Station Museum (Culture & History)

  The Ocean City Life-Saving Station Museum celebrates the history of the U.S. Life-Saving Service, the federal agency established in 1878 to rescue shipwrecked mariners along the Atlantic coastline and the direct forerunner of the United States Coast Guard. The museum offers free seasonal daily programs covering topics including surfman history, beach safety, nautical knot tying, shark biology, and hands-on crafts for younger visitors. A saltwater aquarium room housing live local marine animals including eels, horseshoe crabs, and seahorses rounds out the experience and is a consistent favorite with younger visitors.    

• Fisher's Popcorn (Food & Drink)

  Fisher's Popcorn has been a Boardwalk institution since 1937, when Everett Fisher opened a small stand at the corner of Talbot Street and the Boardwalk and began making caramel popcorn from a secret recipe that has never been altered in nearly ninety years. Every batch is still made by hand in copper kettles, sold by the bucket, and anchored by the signature caramel popcorn made with real butter and brown sugar that has made Fisher's a tradition for generations of OC visitors.    

Reisterstown Main Street offers a mix of historic character, unique shopping, and local favorites in a walkable National Register Historic District. Browse distinctive shops, enjoy signature events like Music on Main Street and the annual Beer and Wine Festival, and pair your visit with nearby trails and small-town charm.    

Local favorites to explore in Reisterstown:    

• Franklin Woodland Trails (Adventure & Nature)

  Franklin Woodland Trails offers visitors a chance to slow down, explore nature, and experience a hidden gem. The trail system winds through mature woodlands with trees that have stood for more than 200 years and provides a welcoming outdoor space for families, hikers, nature lovers, and even four-legged visitors. Along the trails, visitors will find a Story Trail, Children's Discovery Area, outdoor classroom, sound garden, mud kitchen, and other hands-on features designed to encourage exploration, creativity, and learning in nature.    

• Maryland Horse Library & Education Center (Culture & History)

  Located on Historic Main Street Reisterstown, the Maryland Horse Library & Education Center is the largest library of its kind on the East Coast, with thousands of books dedicated exclusively to horses and equestrian history. Visitors can browse an extensive collection covering horse breeds, training methods, riding disciplines, horse sports, veterinary topics, and the rich history of Maryland's equine industry. Officially opened in December 2022, the center serves as a hub for learning, collaboration, and cultural preservation while honoring the important role horses have played in shaping Maryland's heritage.    

• Reter's Crab House & Grille (Food & Drink)

  A longtime Main Street favorite, Reter's Crab House & Grille offers visitors an authentic taste of Maryland's seafood traditions. Known for its steamed crabs, Maryland seafood specialties, fresh oysters, crab soups, and local favorites, Reter's has become a gathering place for residents and visitors looking to experience the flavors that have made Maryland's culinary heritage famous. Reter's is also recognized as a stop on the Maryland Crab and Oyster Trail.    

Downtown Salisbury is a lively Eastern Shore destination where shopping, dining, arts, and entertainment come together in the region’s urban core. Browse local shops and antiques, enjoy galleries and restaurants, and experience the charm of the historic neighborhoods that surround downtown.    

Local favorites to explore in Salisbury:    

• Unity Square (Adventure & Nature)

  A vibrant, centrally located urban park in Downtown Salisbury—situated at Division and Main Streets—designed as the City's first dedicated public gathering space. It features an interactive splash fountain, flexible lawn seating, play areas, a reading garden, public art, and a sculpture. Unity Square hosts seasonal events like Third Fridays, Maryland Folk Festival activities, tree–lighting ceremonies, and more, making it a year-round community hub.    

• The Brick Room (Food & Drink)

  The Brick Room offers more than just a place to grab a drink — it creates an atmosphere people genuinely enjoy being part of. With its cozy exposed-brick setting, craft beverages, live music, and welcoming environment, it gives downtown a unique energy that feels both relaxed and community-oriented.    

• Museum of Eastern Shore Culture (Culture & History)

  The Museum of Eastern Shore Culture celebrates the traditions, stories, and everyday experiences that define Maryland’s Eastern Shore. Exhibits highlight the people, industries, and cultural heritage that make the region unique.    

Sykesville combines small-town charm with a rich railroad and riverfront history, offering a walkable downtown packed with shops, dining, museums, and family-friendly attractions. Explore historic sites and local lore on a walking tour, then plan your visit around the town’s many seasonal events, including the popular Ghosts and Legends tour.    

Local favorites to explore in Sykesville:    

• Black Barn Alpaca (Adventure & Nature)

  As an extension of their working alpaca farm, Black Barn Alpaca’s downtown storefront features visits from live alpacas, giving guests a memorable opportunity to interact with these gentle animals up close. Inside, visitors can explore a curated selection of alpaca fiber goods, learn about sustainable farming practices, and discover the journey from fleece to finished product.    

• The French Twist (Food & Drink)

  This locally loved café is known for its authentic French-inspired pastries, freshly baked breads, and thoughtfully prepared breakfast and lunch options.    

• The Gate House Museum (Culture & History)

  Housed in a historic gatehouse structure that once served the Springfield State Hospital, The Gate House Museum preserves and shares stories of Sykesville’s early development, institutional history, and community life. 

Takoma Park pairs historic character with a creative, eclectic spirit, where Victorian-era charm meets a lively downtown of local shops, art, music, and community events. From the farmers market to the Street Festival and Jazz Festival, there’s always something original to discover in Old Takoma.  

Local favorites to explore in Takoma Park: 

• House of Musical Traditions (Shopping)

  House of Musical Traditions has been a destination for musicians and music lovers for decades. With a focus on acoustic, folk and traditional instruments from the US and around the world, this Takoma Park business carries one of the largest collections of world musical instruments for sale. 

• Soko (Shopping)

  Soko has quickly become one of the most talked-about butcher shops in the DC area, blending an old-school butcher with creative sandwiches. Known for sourcing high-quality local meats from regional farms, the shop built its reputation on carefully selected cuts, house-made specialties, and a strong connection to the local food community. 

• People’s Book (Shopping)

  People's Book is a locally-owned, independent book store and community hub. With an inventory of over 12,000 books, it is easy to get lost in the stacks to find the perfect book. 

Thurmont, the “Gateway to the Mountains,” offers a perfect blend of outdoor adventure and small-town charm near Cunningham Falls and Catoctin Mountain Park. Hike scenic trails, visit covered bridges and orchards, browse local artisan shops, and experience the town’s famous Colorfest each autumn.    

Local favorites to explore in Thurmont:    

• Thurmont Trolley Trail (Adventure & Nature)

  The Thurmont Trolley begins in the heart of Main Street and is a walkable/bikeable trail that takes visitors to the award-winning Thurmont Regional Library. Walkable for all ages and ADA accessible.    

• Thurmont Kountry Kitchen (Food & Culinary)

  Thurmont Kountry Kitchen offers a hometown touch, award-winning homestyle food, and warm customer experience. Family owned for 35 years, 3rd generation.    

• Thurmont Historical Society (Culture & History)

  The Thurmont Historical Society preserves, protects, and celebrates local history for generations to come. Through carefully collected documents, photographs, artifacts, and treasured objects, the museum brings Thurmont’s past to life — its people, places, and culture that shaped the town we know today.    

Westminster offers a walkable downtown where historic character, local shopping, dining, and cultural experiences come together in the heart of Carroll County. Plan your visit around concerts, art shows, and street fairs, and explore nearby attractions like the Carroll County Farm Museum and the Maryland Wine Festival.   

Local favorites to explore in Westminster:    

• City Park Gaming & Brew Room (Entertainment & Events)

  Experience a relaxed, pet-friendly bar offering a wide-ranging selection of local and East-Coast beers, cider, seltzers, and wine. Take your time sipping your beverage while playing a tabletop game. This fun bar offers trivia nights, live music, and special events frequently.    

• JeannieBird Baking Company (Food & Culinary)

  JeannieBird Baking Company creates handcrafted baked goods, pastries, and sweet treats inspired by classic recipes and seasonal flavors.    

• Exploration Commons​ (Culture & History)

  Exploration Commons is an interactive space of the Carroll County Public Library, right in the heart of Westminster's Main Street, where visitors can create using the equipment and resources in the Makerspace, Teaching Kitchen, and Meeting spaces.