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Where to Spend Christmas in Maryland? 11 Movie-Worthy Holiday Getaways
From picture-perfect Main Streets and candlelit villages to mountain retreats and sparkling waterfronts, Maryland has all the makings of a holiday movie. All that's missing is you.
Photo: Tyler Clayton
Photo: Visit Frederick
Photo: @adam_brockett
Photo: Ocean City Dept. of Tourism
Photo: Gaylord National Harbor
Photo: @stadiumswithmysons
Photo: Visit Frederick
Photo: StMichaelsMD.org
Looking for a Christmas getaway in Maryland? Visit Berlin for Hallmark-style Main Street charm, Cumberland for a holiday train ride, Annapolis or St. Michaels for illuminated boat parades, or Deep Creek Lake for a cozy mountain escape. From November through early January, Maryland's towns and waterfront destinations offer seasonal events, festive shopping, and memorable places to stay.
Your Favorite Holiday Movie Brought to Life
Picture it: Snow on the mountains, Main Streets wrapped in twinkling lights, and the faint whistle of a train. In Maryland, the Christmas movie you love most is a real getaway, complete with cozy inns, local shops, and festive traditions.
Just ask the folks in Berlin. The Eastern Shore town was recently named one of 25 finalists in Hallmark's 2026 Merriest Christmas Towns search out of roughly 1,500 submissions.
But Maryland has plenty of other contenders for a starring role. From candlelit villages to waterfront celebrations, here's where to create your own movie-worthy moment this holiday season.
Storybook Main Streets
Some towns seem made for Christmas. Their historic storefronts glow with lights, shop windows beckon with gifts, and town squares fill with neighbors celebrating traditions that have endured for generations.
Berlin: A Real-Life Hallmark Christmas Town
If you've ever wished you could step inside a Hallmark Christmas movie, Berlin is your chance.
The historic Worcester County town has a downtown filled with Victorian architecture, independent boutiques, welcoming restaurants, and a Main Street that practically begs to be photographed.
Holiday decorations and traditions transform the town each winter, but Berlin has another claim to movie fame. The historic Atlantic Hotel appeared in Runaway Bride, starring Julia Roberts and Richard Gere. You can even book the Richard Gere Room.
Browse the shops, settle in for dinner, and spend the night. Berlin is the kind of place where the best discoveries happen when you're in no particular hurry.
Plan Your Movie-Worthy Getaway
- Ice Ice Berlin! — ice sculptures and tree lighting, Nov. 27, 2026
- Shop small, find big treasures — award-winning boutiques and specialty shops
- Christmas Parade — a hometown tradition, Dec. 3, 2026
- The Atlantic Hotel — sleep where Runaway Bride was filmed
- New Year's Eve — Early Bird Ball Drop celebration, Dec. 31 at 6 PM
Downtown Frederick: Main Street by Candlelight
Historic Frederick was made for a holiday stroll.
Its beautifully preserved downtown offers block after block of independent shops, galleries, restaurants, and historic architecture. Spend an afternoon browsing boutiques along Market Street, then wander down to Carroll Creek, where illuminated boats create one of Maryland's most unusual winter displays.
Frederick also does candlelight like few other places. Historic homes, museums, and houses of worship open their doors for seasonal tours. Venture a little farther to Catoctin Furnace for a Traditional Village Christmas, complete with wreathmaking, blacksmithing, and Belsnickel, a rather stern-looking character from German folklore.
Local restaurants, breweries, and charming inns make a weekend especially appealing.
Plan Your Movie-Worthy Getaway
- Floating lights — Sailing Through the Winter Solstice on Carroll Creek, from Nov. 21, 2026
- Christmas by candlelight — Candlelight House Tour, Dec. 5 and 6; Museums by Candlelight, Dec. 12; Historic Houses of Worship tour, Dec. 28
- Meet Kris Kringle — downtown procession, Dec. 11
- Old-world Christmas — wreathmaking, blacksmithing, and Belsnickel at Catoctin Furnace, Dec. 5
- Stay downtown — restaurants, breweries, and charming inns
Leonardtown: A Southern Maryland Christmas
If a holiday movie needs a traditional town square, Leonardtown is ready for its starring role.
The St. Mary's County seat has a handsome historic square anchored by the courthouse, with locally owned boutiques, galleries, restaurants, and gathering places that give downtown its character.
Christmas on the Square brings families together for music, Santa, old-fashioned rides, and holiday traditions. But there's plenty to enjoy beyond the celebration. Shop for locally made gifts, explore Leonardtown's arts scene, and settle in for dinner at one of its downtown restaurants.
For a quieter side of Southern Maryland, venture beyond the square to Leonardtown Wharf, where the waterfront provides a peaceful contrast to the holiday bustle.
Plan Your Movie-Worthy Getaway
- Christmas on the Square — tree lighting and Santa, Nov. 27
- Holiday rides — sleigh rides, train rides, and hayrides
- Shop the square — local boutiques, galleries, and restaurants
- Leonardtown Wharf — waterfront views and quiet strolls
- Stay awhile — Southern Maryland dining and accommodations
Mountain Magic
Up in the Alleghenies, the holidays come with a soundtrack of train whistles and crackling fireplaces. Mountain towns sparkle beneath the stars, snow dusts the ridgelines when the weather cooperates, and historic Main Streets invite visitors to slow down and stay awhile.
Map data © OpenStreetMap contributors
Cumberland and Frostburg: All Aboard for a Magical Ride
Ever wonder what it's like to board the Polar Express™? In Western Maryland, you can ride the officially licensed Polar Express™ Train Ride.
The Western Maryland Scenic Railroad brings the beloved story to life aboard a holiday train that departs Cumberland and travels through the mountains, complete with hot chocolate and a visit from Santa.
Before or after your ride, explore historic downtown Cumberland, once a bustling transportation crossroads. Brick storefronts, locally owned shops, cafés, and restaurants make it easy to linger.
Then head up the mountain to Frostburg, a college town with an old-fashioned Main Street and a rather unusual holiday tradition. During Deck the Meters, residents and businesses turn ordinary parking meters into elaborate holiday creations.
Who knew a parking meter could have so much personality?

Plan Your Movie-Worthy Getaway
- All aboard The Polar Express™! — hot chocolate and Santa, Nov. 21–Dec. 24, 2026
- Historic Cumberland — downtown shopping, cafés, and dining
- Deck the Meters — Frostburg's delightfully decorated parking meters, Thanksgiving week through New Year's
- Storybook Holiday — Frostburg's hometown parade and family festivities, Dec. 5, 2026
- Mountain overnights — cozy inns and accommodations
Deep Creek Lake and Oakland: A Snow-Globe Escape
If your favorite holiday movie ends with a snowy cabin and a roaring fire, Garrett County has your setting.
Start in Oakland, where historic storefronts, independent businesses, and small-town hospitality make holiday shopping a pleasure. Then head toward Deep Creek Lake, a mountain getaway that takes on a different personality when winter arrives.
Spend your days skiing and snow tubing at Wisp Resort or exploring the mountain scenery, and your evenings fireside in a cabin or lodge with winter views.
And if snow doesn't arrive on schedule? There's still a beautiful lake, plenty of good restaurants, and a perfectly good excuse to stay another night.
Plan Your Movie-Worthy Getaway
- A Great Small Town Christmas — holiday festivities in Oakland, Dec. 12, 2026
- Shop local — historic downtown Oakland's independent businesses
- Snow much fun — skiing and snow tubing at Wisp Resort
- Fireside evenings — mountain views and cozy dining
- Cabin getaway — lakeside lodges and winter retreats
Christmas on the Water
In Maryland, even the boats get dressed up for Christmas.
Along the Chesapeake Bay and Atlantic coast, holiday lights reflect off harbor waters, historic waterfront towns welcome visitors, and illuminated boats take the place of sleighs in some of the season's most beloved traditions.
Map data © OpenStreetMap contributors
St. Michaels: A Quintessential Chesapeake Christmas
With its historic streets, independent boutiques, waterfront restaurants, and inviting inns, St. Michaels could pass for a Norman Rockwell Christmas village. Even the bells of Christ Church provide a soundtrack, ringing throughout the year.
At Christmastime, the Talbot County town embraces its traditions with decorated homes, a hometown parade, a holiday marketplace, and the Lighted Boat Parade gliding along the Miles River on Saturday evening, Dec. 12, at 6 PM.
There's plenty to discover between festivities. The Christmas Shop sells holiday treasures year-round, while the Chesapeake Bay Maritime Museum's Hooper Strait Lighthouse dresses for the season.
Add waterfront dining, an afternoon exploring the harbor, and a room at a historic inn, and you have all the makings of a memorable weekend.
Plan Your Movie-Worthy Getaway
- A Rockwell Christmas — hometown parades and holiday cheer, Dec. 10–13
- Let the bells ring — hear the chimes of historic Christ Church
- Christmas year-round — ornaments and treasures at The Christmas Shop
- A lighthouse aglow — holiday magic at the Chesapeake Bay Maritime Museum
- Stay awhile — waterfront dining, boutiques, and charming inns
Annapolis: Twinkling Streets, Waterfront Wonderland
With its centuries-old buildings, narrow streets, independent shops, and working harbor, downtown Annapolis already has the atmosphere of a holiday movie.
The Maryland capital celebrates with decorated storefronts, late-night shopping, seasonal treats, and one of Chesapeake's most spectacular lighted boat parades.
History adds another layer to the experience. Tour the Maryland State House, the oldest state capitol in continuous legislative use, and admire nearby Government House, the governor's official residence.
Then check into one of the Historic Inns of Annapolis, just steps from State Circle. Spend the afternoon exploring Main Street and Maryland Avenue, enjoy dinner overlooking the harbor, and leave time to discover Annapolis after dark.

Plan Your Movie-Worthy Getaway
- Let there be lights! — Grand Illumination, Nov. 29, 2026
- Eastport Yacht Club’s Lights Parade — lighted boats in Annapolis Harbor, Dec. 12, 2026
- Shop after dark — Midnight Madness, Dec. 3, 10, and 17, 2026
- The People's House — admire historic Government House on State Circle
- Step into history — tour the Maryland State House
- Sleep with history — Historic Inns of Annapolis, steps from the State House
Chesapeake City: Christmas Along the Canal
With its colorful 19th-century buildings, inviting restaurants, and waterfront views, Chesapeake City looks as though it was built with a Christmas movie in mind.
This little Cecil County town sits along the Chesapeake and Delaware Canal, where enormous commercial ships occasionally glide past a historic district that seems remarkably unchanged by time.
During the holidays, decorated homes and storefronts bring extra warmth to the streets. Browse locally owned shops, enjoy dinner overlooking the canal, and book a room at one of the town's historic inns.
Chesapeake City rewards travelers who aren't in a hurry. Leave time to explore the historic district and watch the ships go by.

Plan Your Movie-Worthy Getaway
- Christmas on the canal — Lighted Boat Parade, Dec. 5
- Victorian streets — decorated 19th-century homes and storefronts
- Shop small — independent boutiques and specialty stores
- Ships with your supper — canal-side dining and waterfront views
- Stay overnight — historic inns and B&Bs
Ocean City: The Shore in a Whole New Season
You know Ocean City in summer. Now see it sparkle.
The beach resort takes on an entirely different personality when the crowds thin, the temperatures drop, and the Boardwalk belongs to bundled-up walkers rather than beachgoers.
Winterfest of Lights transforms Northside Park into a holiday wonderland with illuminated displays, a towering Christmas tree, and seasonal experiences for the whole family.
By day, bundle up for a winter walk along the beach and Boardwalk, then settle into a cozy off-season restaurant. Book an oceanfront room and enjoy the rare pleasure of having a long stretch of beach almost to yourself.
And since Berlin is just down the road, it's easy to pair the two for a holiday getaway.
Map data © OpenStreetMap contributors
Plan Your Movie-Worthy Getaway
- Winterfest of Lights — Nov. 19, 2026–Jan. 2, 2027
- Northside Park — a 50-foot Christmas tree and Field of Lights
- Hot chocolate, bonfires, and Santa — seaside holiday fun
- Beach and Boardwalk — winter walks along the Atlantic
- Off-season dining — restaurants and oceanfront accommodations
Bright Lights and Big Celebrations
Not every Christmas movie takes place in a quiet little village. Some call for grand displays, dazzling lights, holiday performances, and enough shopping and dining to fill a long weekend.
A Charm City Holiday: Twinkling Lights and Festive Nights
Baltimore turns on the charm for the holidays, with distinctive neighborhoods, colorful traditions, and enough shopping and entertainment to fill an entire weekend.
Start in Mount Vernon, where elegant 19th-century architecture surrounds the Washington Monument. Then head to Hampden, where the residents of 34th Street have turned Christmas decorating into something of an art form. Expect elaborate light displays, fanciful decorations, and Baltimore's beloved pink flamingos dressed in their holiday best.
The European-style Christmas Village fills the Inner Harbor with gift stalls and seasonal treats, while Harbor East offers upscale boutiques, waterfront strolls, and excellent dining.
Add a holiday performance at Meyerhoff Symphony Hall, a visit to the Maryland Zoo, or an evening watching the lighted boat parade along the Fell's Point and Canton waterfront on Dec. 5.
Then check into one of Charm City's luxurious waterfront hotels or boutique retreats. There's no need to squeeze everything into one day.
Plan Your Movie-Worthy Getaway
- Monument Lighting — Mount Vernon's holiday tradition, Dec. 3
- Christmas, Baltimore-style — Hampden's lights and pink flamingos
- European Christmas Village — Inner Harbor, Nov. 21–Dec. 27
- Holidays at the Meyerhoff — Cirque Nutcracker, Dec. 12, and Holiday Pops, Dec. 19 and 20, 2026
- Stay in style — Harbor East dining and boutique hotels
National Harbor: Go Big for the Holidays
Some holiday movies are all about the spectacle, and National Harbor delivers.
Set along the Potomac River, National Harbor combines waterfront promenades, restaurants, shopping, entertainment, and resort hotels in one easy getaway.
At Gaylord National Resort, ICE! transforms enormous blocks of ice into a larger-than-life holiday wonderland, themed this year to Dr. Seuss's How the Grinch Stole Christmas! and open Nov. 14, 2026 through Jan. 3, 2027. Out on the waterfront, a 60-foot Christmas tree lights up the plaza, while the Capital Wheel offers a memorable perspective on the river and surrounding skyline.
But don't stop there. Catch a concert at MGM National Harbor, enjoy the lively atmosphere at Bobby McKey's dueling piano bar, or browse Tanger Outlets and waterfront shops.
With Gaylord National, MGM National Harbor, the Westin, AC Hotel, and other accommodations nearby, there's no shortage of places to spend the night.
Map data © OpenStreetMap contributors
Plan Your Movie-Worthy Getaway
- ICE! — the Grinch-themed Christmas wonderland carved from ice, Nov. 14, 2026 through Jan. 3, 2027
- Lights, camera, fireworks! — waterfront tree show and Saturday night fireworks
- Dinner and a show — concerts at MGM and entertainment at Bobby McKey's
- Shop, sip, and celebrate — Tanger Outlets, waterfront dining, and holiday markets
- Take holiday cheer for a spin — Potomac views from the Capital Wheel
Maryland Holiday Getaway FAQs
Where can you ride The Polar Express™ in Maryland?
The Polar Express™ Train Ride runs on the Western Maryland Scenic Railroad, departing from downtown Cumberland in Allegany County. The holiday train climbs into the Allegheny Mountains with hot chocolate, a reading of the story, and a visit from Santa, and runs on select dates from November 21 through December 24, 2026. Tickets sell out early, so book in advance and plan to stay overnight in Cumberland or nearby Frostburg.
Where can you see Christmas boat parades in Maryland?
Maryland's best-known lighted boat parades are in Annapolis, St. Michaels, and Chesapeake City. The Eastport Yacht Club Lights Parade fills Annapolis Harbor on December 12, 2026; Christmas in St. Michaels brings illuminated boats to the Miles River during its December 10 to 13 weekend; and Chesapeake City's Lighted Boat Parade sails the Chesapeake and Delaware Canal on December 5. Frederick's Sailing Through the Winter Solstice is a stationary display of lighted boats on Carroll Creek rather than a moving parade, and Baltimore's lighted boat parade sails past Fell's Point and Canton on December 5.
Which Maryland holiday attractions continue into January?
Ocean City's Winterfest of Lights at Northside Park runs through January 2, 2027, ICE! at Gaylord National and the nightly tree lighting show at National Harbor run through January 3, 2027, and the Capital Wheel operates year-round. Hampden's 34th Street lights in Baltimore stay lit through New Year's Day, and Deep Creek Lake's ski and snow-tubing season at Wisp Resort runs all winter. Berlin and National Harbor both host New Year's Eve celebrations. Always confirm closing dates on each event's website before you go.
When is the best time to plan a Maryland holiday getaway?
Maryland's holiday season runs from mid-November into early January. Most Christmas parades, candlelight tours, and lighted boat parades take place between Thanksgiving and mid-December, while major light displays continue into the new year.
Do I need to book holiday experiences in advance?
Yes, especially for popular attractions such as The Polar Express™, ICE! at Gaylord National, holiday house tours, and overnight accommodations during major holiday weekends. Check event websites for tickets, schedules, and reservations.
Can I visit more than one destination in a weekend?
Absolutely. Pair Berlin with nearby Ocean City for a small-town Christmas and a winter beach escape. Cumberland and Frostburg make a natural mountain getaway, while Annapolis and St. Michaels offer two distinctive Chesapeake holiday experiences.
Find Your Movie-Worthy Moment
Find a little Christmas magic on a Maryland Main Street, beside a mountain fireplace, or along a waterfront sparkling with holiday lights. Stay for the weekend. Make a memory worth bringing home.
And don’t worry if it doesn’t snow. Even Hallmark can’t guarantee the weather.




