9 Coziest Maryland Towns To Visit In 2025
Despite being only 250 miles long and 100 miles wide, Maryland packs diverse geography and a wide range of possible activities inside its borders. That means its small towns have much to offer in the way of different types of experiences. Maryland's Eastern Shore beach towns, like St. Michaels, let visitors be as busy as they want to be, or just relax in a cozy beach chair with a best-seller. The western part of the state, including Cumberland, boasts breathtaking mountains to climb, hike through, ski down, or relax on a cozy balcony and watch the sun go down. In between are the small towns on the outskirts of the state's largest cities. Each played a role in US history, and all are just waiting for you.
St. Michaels
When you visit St. Michaels, you can stay busy with all the activities the town has going on, or you can relax by resting at the water's edge, listening to the calls of the shorebirds, lost in a good book, watching the people go by, or daydreaming. It's your choice. And that's what makes St. Michaels such a cozy town. Learn about the town's history at the Chesapeake Bay Maritime Museum. Peruse the numerous art galleries, antique shops, boutiques, and coffee shops. Stroll around the town, with homemade ice cream in hand, and watch the osprey soar from their perches.
Take a Patriot cruise on the Miles River, or pilot a rented kayak or SUP. This is a foodie town, and its waterfront restaurants specialize in fresh seafood, from crabs to oysters. Tasting rooms offer many wines, craft beer, and locally made rum. And since you will want to explore the town for several days, stay in a local hotel like the Harbour Inn, Marina and Spa, a cozy B & B, or rent a vacation home and have it all to yourself. An unusually pet-friendly town, pets are welcome nearly everywhere, including in lodging, stores, and more.
Easton
Historic Easton has been described as the cultural center of Maryland's Eastern shore due to the town's many art studios and galleries as well as the nationally recognized Academy Art Museum. It contains over 1,400 pieces in its permanent collection and hosts changing exhibits and programs. Artists from all over the world apply to compete in Plein Air Easton each July, the largest plein air (painting in nature) competition in the US.
Outside the Talbot County Courthouse is a bronze statue of abolitionist Frederick Douglass, one of many sites in the town that showcase his heroism on walking and driving tours. The beautiful downtown has sophistocated clothing boutiques, sporting goods and gear, jewelers, galleries, antiques, home decor shops and more. Treat yourself to a stay at the historic, luxurious Tidewater Inn, a landmark since 1949, recently completely renovated.
Abingdon
This beautiful small town is known as the birthplace of William Paca, a former governor of Maryland and a signer of the Declaration of Independence. Conveniently located just off I-95 in northeast Maryland, Abingdon is a cozy outpost surrounded by unspoiled nature. Visit the Anita C. Leight Estuary Center on Otter Creek, which has programs for kids, adults, and families, like kayak trips through the marshes and tours with a naturalist. Or hike Winter's Run Trail, an easy, fairly flat 2.5-mile out-and-back wildflower walk that typically takes about an hour.
Visit Woodside, a historic 1823 Federal style fieldstone home listed on the National Register of Historic Places. The site also includes a barn, a storage building, and a corncrib. Stop in for a meal at Abingdon Grill or Bushmill Tavern. Stay at Holiday Inn Express & Suites in Abingdon, which has free breakfast and an indoor pool. From Abingdon, it's an easy drive to Baltimore (24 mi.) Philadelphia (78 mi.) and Washington DC (68.6 mi.).
Annapolis
This must-see town boasts both the cozy charm of a college town and the big doings you'd expect in a larger city. Visit the beautiful grounds of the US Naval Academy, located on the Chesapeake Bay waterfront, and take an informative tour that includes the crypt of John Paul Jones below the chapel. The Historic District showcases numerous 18th-century, red brick houses designed in a variety of architectural styles. Along with its naval history, Annapolis has a rich Colonial history as well. Stop at the Visitor's Center for maps to explore on your own, or let Colonial Tours guide you around to the town's historic sites.
The downtown shops have delighted visitors long before other towns revitalized their Main Streets. You'll find maritime souvenirs, clothing, art, antiques, handmade items and treasures for the home. If you feel the love in a crowd, Annapolis hosts many events, including various boat shows in April and October. For a cozy time without masses of other tourists, avoid these shows and busy events like USNA Commissioning Week (May 14-23). The friendly shop merchants, restaurant servers, and hoteliers exude small-town hospitality all year round, however. For breakfasts and lunches made with fresh, local ingredients, at prices that won't clean out your wallet, try Bread and Butter Kitchen on Second Street. Stay at the Historic Inns of Annapolis, three historic inns together with varying amenities.
Havre de Grace
Named by the Marquis de Lafayette because its harbor reminded him of Le Havre, France. The town's location at the Susquehanna River and Chesapeake Bay ensured its history as a vital port, trading center, and a stop on the Underground Railroad. Locals fondly call it HdG (pop. 15,032), hinting at the town's charm and friendly atmosphere. Shops along the downtown streets offer everything from art to antiques and clothing to cozy cafes. Explore the town's history at museums like the Concord Point Lighthouse and Keeper's House Museum and the Decoy and Maritime museums.
Dine on Maryland seafood with a water view at Water Street Seafood or the Promenade Grill. Make plans to come for the 7th Annual Beer and Wine Festival May 10; the Rowdy Rooster Fest on May 16 for art, music, and disc golf; Saturday on the Farm July 12 at Steppingstone Farm Museum; and the Farmer's and Artisans Market yearround, indoors January through April, and outdoors beginning in May. Make it a two-day getaway and take in a show or musical at the Opera House or STAR Centre, then retire to the Vandiver Inn B&B in town.
Cumberland
On the other side of the state, about as far west as you can go and still be in Maryland, is Cumberland. Situated in the Ridge-and-Valley region of the Appalachian Mountains, Cumberland is an outdoor paradise. Hike or bike along the scenic Great Allegheny Passage (GAP) trail that begins in Cumberland and goes all the way to Pittsburgh, PA, and see Cumberland's marker of the Mason-Dixon Line. Or, take the C&O Canal that carried coal and other goods from Cumberland to Washington DC (specifically Georgetown, Virginia) to the Potomac River and ports beyond. Along with nature's majestic scenery, you'll see public art by local artists along the way.
Downtown Cumberland's Arts & Entertainment district is also an art hub. Start at the Allegheny Arts Council, which showcases local artists, musicians, and filmmakers. Check out what's happening on the Western Maryland Scenic Railroad, including scenic rides, murder mystery themes, Winter Express, Santa and more. Try the Corner Tavern & Cafe, where "morning things" are served till 4 pm, ranging from the Pastrami Sunrise to a Veggie Burrito (traditional egg & cheese too). With so much to do in Cumberland, stay a night or two at Cumberland Inn and Spa, set in two 19th-century homes just steps away from the Scenic Railroad and George Washington's early headquarters.
Mt. Airy
Located about 37 miles from Baltimore and 42 miles from Washington DC, Mt. Airy is close enough to visit either city but feels world's away in the countryside. Pick your own fruit at Rock Hill Orchard from June through early November, and enjoy their farmer's market and Woodbourne Creamery's homemade ice cream year-round. Book a table at Black Ankle Vineyards, Elk Run Winery, or Linganore Winecellars for tastings, educational sessions, and live music (typically weekends).
Stop at the Caboose Visitor's Center downtown for the scoop on the town's one-of-a-kind shops selling everything from art and antiques to clothing and confections. Visit Mt. Airy Museum and find out how the B&O Railroad transformed the town from a sleepy stop to a bustling town. Today, the old railroad is a Rails-to-Trails scenic path for walking. Stop at Mount Airy Inn for breakfast all day and wood-fire pizza, and relax for the night at Budget Inn Mt. Airy with cable TV and free Wi-fi.
Middletown
Although not actually in the middle of the state, Middletown is, in many ways, the quintessential US small town. The town sits directly on the National Road, the first government-funded road, which was used by both the Union and Confederate armies during the Civil War en route to the Battle of Antietam. Learn more about the town's history by taking a Heritage Walking Tour downtown. It showcases over a dozen downtown buildings built between 1829 and 1923 and what they have been used for through the years.
Consider timing your Middletown visit with the Snallygaster Festival May 19, Annual Vintage Vehicles in the Valley June 7, Middletown Heritage Festival September 27, Color Me Autumn on October 18, or Christmas in the Valley December 6 for the tree lighting ceremony, Storytime with Mrs. Claus, and a visit with Santa. Sample casual to fine dining downtown at Tapias or Fratellis on Main Street. Stay at Antietam Overlook Farm in nearby Keedysville or 10 Clarke Place B&B in Frederick.
Catonsville
The small dot on a Maryland map does not begin to give a clue to what visitors will find in Catonsville. "Music City Maryland," the title bestowed on the town by the state's General Assembly, is an apt description. The Arts District is filled with original music treasures, from stores like the Appalachian Bluegrass Shoppe to Guitar Exchange, sites for bands to practice and experts in post production who help musicians pull it all together. Each retailer has their own vibe and specialty, and serves national as well as international customers while maintaining their small-town, cozy charm.
Take a picnic to Benjamin Banneker Historical Park and Museum and learn about the African-American scientist through interpretive exhibits, a split-log cabin, a 19th-century farmhouse, Colonial gardens and more. Also check out Trolley Line #9 Trail, a paved, 1.25-mile stretch that runs from Catonsville to Main Street in Ellicott City, converted as part of the Rails-to-Trails program. Consider dining in at The Beaumont for jumbo lump crab cakes or duck confit, then relax at Holiday Inn Express Baltimore West, just steps away from the downtown and Arts District activities.
From Cumberland in the northwest part of the state to Easton on the Eastern Shore, Maryland has no shortage of cozy, small towns to visit. Which ones appeal to you most depends on your interests and perspective. Many Maryland towns were founded in Colonial times and have rich Revolutionary War beginnings. Most saw their town's buildings become hospitals and headquarters during the Civil War. They have grown and evolved to become artistic enclaves, like Catonsville for music and Cumberland for art. Perhaps Maryland's best feature is its size. The 9th smallest US state makes it possible to travel it from end to end, catching its breathtaking beauty and vast array of adventures in between.
