Maryland's 9 Most Festive Downtowns For The Holidays
When the air turns colder, Maryland's smaller downtowns shine in entirely different ways than those found in the bigger cities. Historic streets, waterfront promenades, and community-sized holiday events all combine to create a cozy yet festive experience. Discover nine small towns, where the downtown areas exude charm, tradition, and a wealth of activities to enjoy during the holiday season. Consider this your map of small-town holiday magic in the Old Line State.
Annapolis
Annapolis sits at the mouth of the tidal waters of the Severn River, just above the Chesapeake Bay. Founded in the 17th century and serving as Maryland's colonial capital briefly after the Revolutionary War. With its colonial-era buildings and the historic Maryland State House, the downtown area invites strolling through centuries of architecture. During the holiday season, the waterfront takes center stage, where you can walk along the City Dock and Spa Creek to watch the Eastport Yacht Club Lights Parade of illuminated boats.
Beyond the boat parade, you will find the downtown tree-lighting on State Circle, and the "Midnight Madness" shopping nights when Main Street, Maryland Avenue, and West Street stay open late for deals, festive treats, and live music. Dine at waterfront spots like O'Brien's Oyster Bar & Seafood Tavern and then take a carriage ride through the historic district.
Easton
Set on Maryland's Eastern Shore in Talbot County, Easton offers a quiet elegance, characterized by its courthouse circle, well-preserved homes, and historic storefronts. Heritage and culture blend seamlessly into the downtown fabric. In December, Harrison Street and Goldsborough Street will be transformed for the holidays. Visitors can browse independent bookstores, art galleries, and boutique shops, then stroll into the Academy Art Museum for seasonal exhibits. The Festive of Trees exhibit also showcases decorated trees from local organizations, and the Prager Family Center for the Arts presents a seasonal show.
The town's holiday parade winds its way through downtown with floats and local bands after the tree-lighting ceremony at Thompson Park. Late-night shopping nights bring free carriage rides in front of the Visitor Center and carolers roaming the street. Finish your evening with dinner at the Tidewater Inn's fire-lit dining room or sip craft cocktails at the pop-up bar they host during holiday events.
St. Michaels
On the Miles River in Talbot County, St. Michaels was once a shipbuilding and maritime center. Its downtown retains a maritime feel with its narrow streets, weathered clapboard buildings, nautical touches, and docks full of small craft and sailboats. The campus of the Chesapeake Bay Maritime Museum is situated along the waterfront, spanning 18 acres and featuring historic vessels, the 1879 Hooper Strait Lighthouse, and exhibits on the lives of watermen and boat restoration.
During the holidays, the town comes alive with its "Christmas in St. Michaels" weekends. The Chesapeake Bay Maritime Museum often runs special winter displays, while Main Street hosts a holiday craft market for artisanal gifts. You will find horse-drawn carriage rides through the downtown, and historic homes open for guided tours under soft lighting. For dining, stop by the iconic The Crab Claw Restaurant for fresh Maryland blue crab and waterfront views. At dusk, be sure to watch the waterfront reflections of colorful holiday lights, which create a postcard-perfect scene.
Ocean City
Ocean City is Maryland's classic Atlantic beach resort town, but in the colder months, Ocean City transforms into a surprisingly charming holiday getaway. Visitors can explore the Life-Saving Station Museum, which showcases the town's maritime history, take a bay-sunset walk along the downtown boardwalk area, or shop for gifts in boutique stores off the main strip. The familiar Atlantic Ocean backdrop, paired with holiday lights, fewer crowds, and a relaxed pace, makes this seaside town worth visiting.
The big draw is the "Winterfest of Lights" at Northside Park, featuring 58 acres of walk-through displays with thousands of twinkling lights and animated holiday scenes that create a winter wonderland. The event features an interactive 50-foot giant Christmas tree, themed zones such as "Candy Cane Lane" and "Fire & Ice Village," and horse-drawn carriage rides during "Enchanted Evenings." Downtown along the boardwalk, you will find themed weekend events with holiday food specials, lighted parades geared toward families, and boutiques that stay open for seasonal shopping. A boardwalk stroll at dusk under the colorful string lights offers a contrast of Atlantic breeze and holiday sparkle.
Pair that with dinner at a seafood restaurant, like Harrison's Harbor Watch, or Thrasher's Fries, which is famous for its vinegar-drenched fries, still open for the season, and you have a beach-town holiday with a twist. If the weather allows, take a magical nighttime winter beach walk.
Berlin
Berlin, on Maryland's Delmarva peninsula, boasts beautifully preserved Victorian architecture, independent art galleries, and a strong downtown identity. The town is officially designated as an Arts & Entertainment District, which means you will find art galleries, live-music venues, and shops run by local makers. Come and embrace the old-fashioned community spirit this holiday season in Berlin.
Main Street becomes a hub of holiday festivity. The earliest event is Ice Ice Berlin & Tree Lighting, held in late November. Expect to see hand-carved ice sculptures along Main Street and the lighting of the town's Christmas tree in front of the historic Atlantic Hotel. The main event is the Berlin Christmas Parade, which winds down Main Street with over 80 floats, dancers, fire trucks, and Santa Claus, passing decorated antique shops and cafés that offer hot cocoa and cookies.
Shops, such as Honey Water Candles or The Greyhound indie bookstore, stay open late for special holiday nights, and carriage rides are offered along the street. Enjoy a meal at Blacksmith or Oaked at the Globe in one of the town's restored historic buildings. A short drive takes you to nearby Assateague Island for a winter beach walk and perhaps wild-horse spotting, rounding out the nature-minded side of your visit, if you want.
Havre de Grace
Located where the Susquehanna River flows into the Chesapeake Bay, Havre de Grace seamlessly blends its history as a river port and rail hub with small-town waterfront charm. Its downtown promenade, Main Street Victorian homes, and waterfront boardwalk give it a maritime character. The town is home to the Concord Point Lighthouse, one of the oldest on the Bay, and boasts a rich past in shipbuilding and rail transport. The downtown is also part of an Arts & Entertainment District, with galleries and specialty shops lining Washington Street and Pennington Avenue.
The town's signature holiday attraction is the Holly Jolly Parade and the tree lighting in the downtown center. Another standout is the Candlelight Tour, organized by the Lock House Museum, where historic homes, churches, and inns across downtown open their doors for a night of decorations, music, and candlelit ambiance. After dusk, stroll the riverfront boardwalk to view lights reflected on the water, then browse artisan and specialty shops on Congress Avenue. Dine in riverside restaurants that serve Chesapeake Bay crab cakes or steamed oysters.
Chestertown
Chestertown is a colonial port town on the Chester River, known for its 18th-century architecture and vibrant cultural events. Its historic downtown district is full of brick-lined streets, historic homes, and a legacy of maritime and academic life (Washington College is nearby). The town has preserved its character with independent shops, art galleries, and a strong sense of community spirit.
In December, the town hosts the "Dickens of a Christmas" festival. Charles Dickens' 1840s London comes alive with costumed performers roaming on High Street and Main Street, horse-drawn carriage rides pass by wreath-adorned colonial homes, and vendor stalls sell handmade gifts and holiday treats. You can tour historic houses, wander through streets lined with lights, and then pop into a local waterfront restaurant for seasonal fare.
Leonardtown
Leonardtown, the county seat of St. Mary's County, centers its downtown around a compact square, flanked by civic buildings, art galleries, and locally owned restaurants, that is easy to explore on foot. The town is officially recognized as the only designated Arts & Entertainment District in Southern Maryland. A neat shopping experience awaits at Shepherd's Old Field Market, featuring artisan vendors, a beer garden, and specialty foods.
The main holiday attraction is the "Christmas on the Square" celebration. A large tree lighting on the town square, live music, children's craft activities, hot cocoa stands, and horse-and-carriage rides through the adjoining streets. Galleries stay open late for shopping, art studios often feature holiday pop-up shows, and the local restaurants offer seasonal menus.
Frostburg
Frostburg is a mountain-town gem in Western Maryland, anchored by quaint downtown streets and a lively arts scene thanks in part to Frostburg State University. The downtown area is lined with historic architecture tied to the 19th- and early-20th-century rail and coal industries, featuring independent boutiques, cafés, and bars. The downtown retains a sense of grit and vintage charm.
During the holiday season, Frostburg hosts a Victorian Christmas weekend. Craft markets fill storefronts, a tree lighting ceremony takes place on Main Street, and seasonal concerts fill the local university's venues, while downtown merchants decorate their windows with holiday themes. Wander along Fayette Street and Main Street, pop into the independent bookstores or bakeries, and if snow permits, take a short winter hike on nearby trails.
Each of these nine Maryland towns brings its own flavor of holiday cheer, from waterfront lights and boat parades to Victorian house tours, carriage rides, and art-filled downtown squares, as well as community tree-lightings, all happening this holiday season. No matter which Maryland town you pick, like the maritime sparkle of Annapolis, the gallery-filled calm of Easton, the beach town of Ocean City, or the quiet square of Leonardtown, there is a holiday experience for everyone. Pick a town, check its event calendar, and head in for a holiday visit that will be both local and memorable.
