Berlin, Maryland Won America’s Coolest Small Town in 2014. 8 Reasons It Still Earns the Title in Winter

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Ocean City empties out after Labor Day, but eight miles inland, a small town keeps its lights on all winter. Berlin Maryland in winter is a historic Main Street, a Victorian hotel, a Christmas parade, and a calm base for the barrier islands, and it is the same town that beat out 14 other finalists for a national title more than a decade ago.

Berlin won Budget Travel’s America’s Coolest Small Town contest in 2014. According to Budget Travel, the town, with a population of 4,563 at the time, took more than 28 percent of the votes among 15 finalists, receiving 39,285 votes out of 137,819 cast. Cazenovia, New York, finished second. The magazine praised Berlin as “a truly spectacular place to visit or put down roots.”

Titles like that are easy to win in a popular summer town. The better test is whether a place is still worth visiting in December, when the beach crowds are gone. Berlin passes. Here is why.

8 Reasons Berlin Still Earns the Title in Winter

Each of these is a specific reason to make the drive between November and March.

1. A Walkable Historic Main Street

Berlin’s downtown is a National Register historic district, and most of what you want to see is within a few blocks of the intersection of Main Street and Broad Street. Brick and frame buildings from the 1800s and early 1900s hold shops, restaurants, and galleries. In winter, the sidewalks are calm, parking is easy, and you can walk the whole downtown in under an hour, then spend the rest of the day going in and out of the shops.

2. The Atlantic Hotel, Built in 1895

The Atlantic Hotel at 2 Main Street is the town’s landmark. Built in 1895, it has been restored with Victorian decor and a wide front porch with rocking chairs. Even in winter, it is the anchor of downtown. You can stay overnight, have a drink, or just walk in to see the lobby. During the holidays, the hotel and the buildings around it are decorated, and the porch becomes a favorite photo spot.

3. The Calvin B. Taylor House Museum

This 1832 house on Main Street is the town’s history museum, named for a local banker and businessman whose family lived there. It holds exhibits on Berlin’s past, period furnishings, and artifacts from the town’s early days. It is a small museum and a good one-hour stop. Hours are seasonal, so check before you plan around it.

4. The Christmas Parade on December 3

Berlin’s Christmas Parade is one of the biggest events of the winter. The town lists the 2026 parade for Thursday, December 3, at 7 p.m. Local businesses, schools, fire companies, and nonprofits parade up Main Street, typically about 80 participants, and judges award prizes in several categories. It is a small-town parade in the best sense, with bands, decorated floats, and fire trucks covered in lights.

• Arrive early: Main Street fills by 6:30 p.m.
• Dress warm: Early December evenings near the coast are often in the 30s and 40s.
• Stay after: Many shops and restaurants are open late on parade night.

Berlin also holds other holiday events in December, including a tree lighting and seasonal shopping nights. Check the town’s special events page for the full schedule.

5. You Can See Where Hollywood Filmed

Berlin has had two big movie moments. The 1999 romantic comedy “Runaway Bride,” starring Julia Roberts and Richard Gere, was filmed in and around the town, which stood in for the fictional town of Hale. The 2002 film “Tuck Everlasting,” with Sissy Spacek, William Hurt, and Ben Kingsley, was also shot there. Fans still come to find the locations. Main Street, the Atlantic Hotel, and nearby blocks are instantly recognizable from “Runaway Bride.”

6. Independent Shops for Holiday Gifts

Berlin’s downtown is made up mostly of locally owned shops: boutiques, gift shops, antiques, art galleries, bookstores, and specialty food stores. That makes it a good place to do holiday shopping without a mall. Many shops stay open on weekends year-round and extend hours in December. Small-business shopping events on the weekend after Thanksgiving draw local crowds.

7. Local Food and Beer

Berlin has a lively food scene for a town its size. Downtown restaurants range from casual cafés and sandwich shops to sit-down dinner spots. Burley Oak Brewing Company, a craft brewery in town, has a taproom that is a regional draw. Seafood from the Eastern Shore shows up on many menus, and winter is oyster season. Expect lunch to run about $15 to $25 per person and dinner about $30 to $60.

8. A Quiet Base for Assateague and Ocean City

Berlin sits about 8 miles west of Ocean City and about 10 miles north of the Maryland entrance to Assateague Island National Seashore. In winter, many Ocean City businesses close or reduce hours, but the boardwalk and beach are still there to walk. Assateague’s wild horses are easier to see in winter, when crowds and bugs are gone. Staying in Berlin gives you a historic town to come back to at night instead of an empty resort strip.

Why Berlin Won in 2014

Budget Travel’s contest was a public vote among 15 finalists chosen from reader nominations. Berlin’s win came from an organized local effort and a town that had worked for years to revive its downtown. The town’s government celebrated the win on February 25, 2014, the day voting ended.

The win brought a wave of visitors and press. More than a decade later, Berlin still uses the title in its marketing, and it has kept the things that made it popular: a walkable downtown, independent businesses, and community events.

What Has Changed Since 2014

Berlin is busier than it was in 2014, especially on summer weekends, and some locals have mixed feelings about the growth. Home prices have risen with demand for the Ocean City area. But the core downtown is still small and locally owned, and winter is when it feels most like the town that won the vote.

Where to Stay

• The Atlantic Hotel: The historic option on Main Street. Winter rates are often lower than summer rates, but they vary.
• Inns and B&Bs: A few small inns operate in and near town.
• Chain hotels: Along Route 50 and Route 113, often $90 to $160 a night in the off-season.
• Ocean City: Hotels and condos drop to very low off-season rates, sometimes under $100 a night, and are a 15-minute drive away.

Getting There

Berlin is on Maryland’s Eastern Shore, close to the Delaware line.

• From Washington, D.C.: About 145 miles, usually 2.5 to 3 hours via Route 50 and the Chesapeake Bay Bridge.
• From Baltimore: About 140 miles, roughly 2.5 to 3 hours.
• From Philadelphia: About 140 miles, usually 2.5 to 3 hours via I-95 and Route 113 or Route 1.
• Bay Bridge traffic: The Chesapeake Bay Bridge is much easier in winter than in summer, when weekend backups are common.

A Sample Weekend: Berlin Maryland in Winter

• Friday evening: Check in at the Atlantic Hotel or a nearby inn. Dinner downtown.
• Saturday morning: Walk Main Street and Broad Street. Visit the Taylor House Museum if open.
• Saturday afternoon: Drive to Assateague Island to look for wild horses and walk the beach.
• Saturday evening: Burley Oak’s taproom or a downtown restaurant. Holiday lights on Main Street.
• Sunday: Walk the Ocean City boardwalk in the quiet season, then head home.

Winter Weather in Berlin

Berlin sits close to the Atlantic, which keeps winters milder than in much of the Mid-Atlantic. Daytime highs in December and January are often in the 40s, with nights near or below freezing. Snow falls some winters but rarely lasts long. Wind off the ocean can make the beach feel much colder than town, so bring a warm jacket, a hat, and gloves for Assateague and the boardwalk.

Tips for a Better Winter Visit

• Check business hours: Some shops and restaurants close one or two days a week in the off-season.
• Book parade-night rooms early: Lodging in town fills for the Christmas parade weekend.
• Shop on weekends: Weekends have the most shops open and the most holiday events.
• Bring binoculars: For wild horses and winter birds on Assateague.
• Eat local seafood: Ask about oysters and local fish, which are at their best in the cold months.

Who Berlin Suits Best

Berlin works well for couples who want a walkable small-town weekend, families who want a low-key holiday outing, and anyone who likes the beach but not beach crowds. It is less suited to travelers looking for nightlife, which is limited in winter.

The Bottom Line

Berlin won America’s Coolest Small Town in 2014 with a vote powered by local pride. In winter, you can see why: a walkable downtown, the 1895 Atlantic Hotel, a small museum, a Christmas parade on December 3, movie history, independent shops, good food and beer, and easy access to the beach and wild horses. The summer crowds leave. The town stays.