These Towns in Maryland Come Alive in Winter

Winter is a season of both snow and giving, alongside spending time with close friends, family, and lovers. Maryland has an excellent sense of community and closeness among its residents, with the later months of the year being special for anyone who lives here. When the snow falls, events are everywhere in the state as people come out to celebrate this spectacular time of year. Parades line the streets in places like Chestertown and towns like Saint Michaels encourage people to have the greatest holiday display, making for a lovely street view every night during the season. Visit one of the many towns that come alive in winter with decorated trees and street corners like Ocean City or Cumberland and take a stroll!

Saint Michaels

The town of Saint Michaels glows during the winter months, starting off with a yearly tradition called "Light up the night," where residents are encouraged to have the greatest display of decorations outside of their homes. Hundreds of houses are beautifully lit up, with the best of them listed on the town's website every year.

The annual holiday event "Christmas in St. Michaels" helps fundraise money for local non-profit organizations in town and is usually held over a weekend in early December. Happenings during this weekend include a breakfast with Santa, two different displays called the Lighted Boat and Talbot Street Parade, respectively, and music throughout the month from both the Union United Methodist Church and the Mid-Shore Community Band, with the latter performing before the Talbot Street Parade. A dedicated parking lot off South Talbot Street leads to the St. Michaels Nature Trail, which travels through the woods around town and passes by abandoned railway tracks. This paved trail is perfect for admiring the winter beauty!

Ocean City

Ocean City is an Atlantic resort town offering amazing oceanside views, especially during the year's later months. The town commemorates both the holidays and the winter season through Winterfest, short for Winterfest of Lights in Northside Park. The festival has been going strong for over three decades, with new displays and decorations every year. Some of the more famous attractions are the 50-foot tree, Santa Claus's Reindeer, 12 Drummers Drumming, and a designated "selfie spot" in front of a large engagement ring on the boardwalk. There's even a tram to make exploring the whole park easier!

Other festive events that bring the town to life are the annual Ocean City Christmas Parade, with floats and elves dressed up strolling down the street, a run called the Winterfest of Light Jingle Bell 5K Race, and even SantaCon, which starts with a party at Pickles Pub on Philadelphia Avenue, where hundreds of Santas come to socialize over a weekend with food and drinks across town and on the boardwalk. The event has raised money for different charities over the years.

Rock Hall

In the heart of the Chesapeake Bay region is the quaint town of Rock Hall, right on the water. It got its start through its harbor, where a lot of the economy is still present today, with commercial boating and watermen being present throughout the year. Winter is very close to the people of this waterfront town, with many events listed on their website throughout the season. In late November, the town hosts Rock Hall Home for the Holidays, which sets off the season with holiday shopping offered throughout the town.

December especially has a myriad of fun opportunities that tie the community together, like multiple cookie parties where people decorate and bake yummy treats at the SDA Church, and ugly Christmas sweater parties at both Waterman's Crab House and SGT Preston Ashley American Legion on Sharp Street. Join the community bonfire in mid-December at the Raum Chapel to warm up and get free snacks. Just remember to bring your own chair! Lodging places like Osprey Point offer water and snow views, which are unforgettable this time of year.

Chestertown

Chestertown likes to celebrate the start of winter with fresh oysters at the Dickens Festival in December! If you miss the festival, they are in season and can be enjoyed all around town to help bring in that holiday mood at restaurants like the Retriever Bar. There are also plenty of historic buildings like the Denton House, Widehall, or Hynson-Ringgold House that bring out their festive spirit with lights and other such ornaments.

Every year, the town is covered head to toe with fun family events like RiverArts, a show alongside holiday gifts made by local artisans and artists, the concert "Meet You at the Movies" by the Chester River Chorale, which has a collection of songs from holiday films, and the Chestertown Farmers Market featuring fresh winter veggies and so much more! Visitors also often enjoy making wreaths and having wine alongside an art walk, which features local artists and live music on Main Street.

Cumberland

Winter months can be some of the best times throughout the year to try something new. In 2023, Cumberland is hosting their first annual Winter Festival and Market, which features both an artist and retail market alongside free gift wrapping, making gift-giving during the holiday season effortless. Games, live music, and a bike decorating contest are also available.

The town has this week-long festival alongside many other events throughout the season, including painting and craft opportunities at Mr. Toad's Pottery, where people can make their own soup mugs for the holidays and color them, an ugly sweater party at Fore Axes, where people can have winter drinks and throw axes, concerts, a tree lighting on Baltimore Street in late November, and so much more! One of the most stunning ways to see the winter landscapes is by going on a train ride through the Western Maryland Scenic Railroad, which can include a three-hour round trip from Cumberland to Frostburg.

Berlin

The town of Berlin in the east of Maryland has a deep connection with its history, with the Berlin Commercial District housing many 19th-century commercial and residential buildings that still stand today, like the Burley Manor and the Chandler house. The town is picturesque to the point where it was the filming location of not one but two motion pictures: Tuck Everlasting and Runaway Bride.

In town are both Heron Park and Stephen Decatur Loop, which are both close by and have wonderful views of their respective parks during the winter. Berlin celebrates the lighting of its 20-foot tree downtown in November with an annual ice sculpture showcase called Ice Ice Berlin. Meanwhile, in December, there is a Christmas Parade led by local organizations, which features marching bands, dancers, and the local fire stations. By the end of the year, after the snow has fallen and piled up nicely, a New Year's Eve celebration is held around Main Street, with separate time frames for kids and adults to enjoy the start of the new year.

Frostburg

One of the best winter wonderlands in Maryland is Frostburg. With a name so festive, it is no wonder that the town tries its hardest to welcome in the colder months of the year. The Sunday after Thanksgiving features a tree-lighting ceremony in town, with free cookies and hot cocoa alongside carriage rides. On the first Saturday of December is Frostburg's largest event: Storybook Holiday! Many varied activities are available during the day and night, including book reading for children, a parade with both Santa Claus and Jack Frost, and other holiday delights like the Elf Olympics.

Holiday shoppers love looking for gifts in the town's annual Shop Small Holiday Market, which helps more local businesses. Frostburg is also another access point to the Western Maryland Scenic Railroad for people who want to ride on the Polar Express! Going through Frostburg all the way to Cumberland is the Great Allegheny Passage, which is a continuous trail that runs around 16 miles from the town to its end destination. It's mainly covered in limestone, which makes for easy walking, especially during the winter, when snow lies everywhere.

While Maryland isn't viewed too much as a coastal state, there certainly is a lot of culture and history revolving around its positioning near both the Atlantic Ocean and the Chesapeake Bay. Winter in this part of the country revolves around cold weather, snow, and seafood! Where besides Maryland could you find oysters alongside a Christmas tree lighting? It's perfect for anyone who wants to spread holiday cheer and be right on the water at the same time.