View of Chesapeake City, Maryland, from the Chesapeake City Bridge, showing the town's waterfront, historic buildings, and boats along the canal.

9 Slow-Paced Towns to Visit in Maryland

From its western mountain border to its coastal Eastern shore, Maryland is home to vibrant cities, but it also offers a variety of peaceful, quaint, slower-paced towns where life feels more relaxed. These smaller communities provide the perfect escape from the hustle and bustle of everyday life. Smaller, slower-paced towns do not have to be boring, however. The following towns in Maryland are full of things to do but at a slower pace of life.

Oakland

A vibrant autumn scene at Swallow Falls State Park in western Maryland, with colorful foliage in shades of red, orange, and yellow surrounding the cascading waterfalls and rocky terrain. The crisp air and rich colors create a picturesque setting.
A vibrant autumn scene at Swallow Falls State Park in western Maryland.

The westernmost town in the state, Oakland is a small town with just under 2,000 residents. Oakland offers visitors a beautiful historic area in which to wander and explore. It was named a Designated Main Street in 1998, meaning that it has an appealing cityscape; economic vitality; offers events year-round; is clean, safe, and green; and is marketed and promoted well.

The county seat of Garrett County, Oakland, houses the Garrett County Historical Museum, which houses artifacts from the area. It also is home to the Garrett County Transportation Museum, showcasing vehicles of all types.

Oakland sits at an elevation of 2,451 feet in the Appalachian Mountains and embodies the peaceful beauty of a mountain town. Its mountain location also means that world-renowned skiing, in season, is available at nearby Wisp Resort.

Outdoor enthusiasts will love that two state parks, Swallow Falls State Park and Herrington Manor State Park, are located within Oakland. Swallow Falls features the 53-foot Muddy Creek Falls, along with miles of trails and campsites. A 5.5-mile trail links Swallow Falls to Herrington Manor, where visitors will find the 53-acre Herrington Lake, log cabins, and trails. Additionally, Oakland is adjacent to Deep Creek Lake, a 3,900-acre man-made reservoir that is a popular tourist attraction.

Oakland may be slow-paced, but it offers its share of restaurants, one of the most notable being Brenda's Pizzeria, with its famous Abbondanza pizza measuring 26 inches. Those who prefer simpler food might opt for the old-time lunch counter and soda fountain located within Englander's antique store. Just remember that it is only open for breakfast and lunch.

Easton

The corner of Dover and Harrison Streets in Easton, Maryland, on the Eastern Shore, featuring historic buildings, quaint shops, and a peaceful small-town atmosphere on a summer day.
The corner of Dover and Harrison Streets in Easton, Maryland. Editorial credit: JE Dean / Shutterstock.com

With a population of just over 17,000, Easton is a small historic town situated at the headwaters of the Tred Avon River in Maryland's tidewater region. Once the Colonial Capital of the Eastern Shore, guided walking tours of the downtown area are offered on the third Saturday of each month. These tours focus on exploring the Market House, Bullitt House, and Methodist Episcopal Church. Visitors can take self-guided tours of the area whenever they like, appreciating the Colonial and Victorian architecture throughout the town.

Those looking for culture will enjoy the Avalon Theatre, started in 1922 and known as one of the US' finest Art Deco theatres. The theatre hosts a variety of concerts and events year-round.

Easton is also home to one of the oldest free African American neighborhoods in the US, The Hill Community. This was a community of African Americans freed from slavery before the Civil War's end. Today, visitors can walk through the community and hear stories about the men and women who once lived there.

Easton offers many culinary choices, from the simple Amish Country Farmers Market with its baked goods, produce, meats, and casual dining to the upscale Bas Rouge, a Euro-style fine dining restaurant with a world-class wine list.

Chesapeake City

View of Chesapeake City, Maryland, from the Chesapeake City Bridge, showing the town's picturesque waterfront, historic buildings, and boats along the canal.
View of Chesapeake City, Maryland, from the Chesapeake City Bridge.

Although Chesapeake City's population is a bit under 800, do not let its small citizenry fool you. There is still much to do in this sleepy town along the Chesapeake and Delaware Canal, the only Maryland town that is located along a working commercial canal.

Upon the completion of the canal in 1829, the town of Chesapeake City began to take shape. Today, visitors can explore its historic area; the many Victorian buildings still standing in the town are home to art galleries, antique stores, clothing stores, and gift shops.

Those looking for outdoor entertainment will enjoy the summer concerts and events offered in Pell Gardens, the town's park located in the downtown area. The park honors Dr. Walden Pell and his wife, Edith, who helped in the restoration of town buildings in the 1970s.

Its location on the canal provides many opportunities for visitors to sit on the decks of the town's restaurants and bars and enjoy outdoor music. Famous eateries on the water include Schaefer's Canal House, Chesapeake Inn Restaurant & Marina, and the Bayard House Restaurant. Local seafood, fine wine, and good times can be had at each of these establishments.

Chestertown

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland, showcasing historic buildings, tree-lined streets, and the waterfront along the river, all set against a backdrop of lush greenery.
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland.

Located in Kent County, Chestertown is home to just over 5,500 people. It was founded in 1706 along the banks of the Chester River on Maryland's Eastern Shore. Today, Chestertown houses the Historical Society of Kent County, which gives visitors a peek inside what life was like during the town's founding days. The Historical Society of Kent County offers a revised and updated self-guided walking tour of the Chestertown Historic District.

Chestertown is also home to Washington College, the first college chartered in the sovereign US. In addition to higher education, Chestertown offers visitors a vibrant downtown area full of over 200 art galleries, culture, shops, restaurants, and bars.

Events occur in Chestertown year-round and include the Annual Chestertown Jazz Festival, held in Wilmer Park every September; the Sultana Education Foundation's Downrigging Weekend Festival each November; the Winter Art Walk in December; and a Dickens of a Christmas in December.

Food and drink choices in Chestertown include Bad Alfred's Distilling Co., Casa Carmen, Phat Daddy's BBQ, the Kitchen at the Imperial, and Watershed Alley. These restaurants and bars offer locally raised beef, seafood, and locally distilled liquors.

Mount Airy

The Mt. Airy house in Sharpsburg, Maryland, a historic home set in a rural landscape
The Mt. Airy house in Sharpsburg, Maryland. By Acroterion, CC BY-SA 4.0, Wikimedia Commons

With a population just under 10,000, Mount Airy is a small town located in Carroll and Frederick Counties, part of both the Washington and Baltimore Metropolitan Areas. Although the town is within 40 miles of both cities, it still retains its small-town feel, away from the hustle and bustle of urban areas.

Wine and beer connoisseurs will not want to miss tours of popular wineries and breweries in Mount Airy. Red Shedman Farm Brewery is a family owned and operated 15-barrel brew house, craft brewery, and hop yard, featuring beer and hard cider. Linganore Winecellars, the largest winery in Maryland, is home to Maryland's first Americana Viticultural Area. It offers over 30 wines produced using eco-friendly methods.

The Mount Airy Museum is located within the Mount Airy Statin on Main Street, and features artifacts dedicated to preserving the town's past. The town's walkable district features shops, restaurants, and more housed within historical buildings in the downtown area.

Dining options in Mount Airy include the Mount Airy Inn, featuring Maryland seafood; CarterQue Barbeque & Grilling Co., a popular spot; and Tony Pazzo Italian Ristorante and Bar, offering restaurant-style Italian food with a pizza joint vibe.

Havre de Grace

Aerial sunset panorama of Havre de Grace, Maryland, with an orange sky and clouds reflecting on the Susquehanna River and Chesapeake Bay.
Aerial sunset panorama of Havre de Grace, Maryland.

Havre de Grace is home to just under 15,000 people. Incorporated in 1785, the town, whose name means "harbor of grace," is situated where the Susquehanna River meets the Chesapeake Bay. Historic Havre de Grace is on the National Register of Historic Places. Self-guided walking tours of the area are available by stopping at the Visitors Center in town.

Guided tours of the Concord Point Lighthouse are also available from April through October. Visitors must be at least 42 inches tall to climb to the top of the lighthouse. The Lafayette Trail Tour is another self-guided app tour that is offered. It is a three-mile loop through the town indicated by "Walk the Lafayette Trail" signs along the way. The tour can be downloaded on mobile via the Distrx app.

Havre de Grace is not just for history buffs, however. As one of 25 designated Arts and Entertainment Districts across Maryland, the town houses a variety of art galleries, museums, and arts and entertainment venues for live events. The town's walkable shopping district also offers boutiques, gift shops, antiques, collectibles, novelties, and more.

Dining and beverage options in the downtown area are diverse and include Abbey Burger, Bella's Tea Room, Concord Point Coffee, La Cucina Italian Restaurant, and MacGregor's Restaurant, located beside the waters of the Susquehanna River.

North East

A view of a main street in the quaint small town of North East, Maryland, on August 19, 2022. The street is lined with charming shops and historic buildings, reflecting the town’s relaxed atmosphere in Cecil County.
A view of a main street in North East, Maryland. Editorial credit: George Sheldon / Shutterstock.com

Although North East's population totals just over 4,000 residents, the town comes to life in the summer months when tourists flock to its prime location on the North East River, swelling its numbers. Many are also drawn to the town's proximity to Philadelphia and Baltimore, each of which are about an hour's drive.

North East was Cecil County's first permanent settlement, settled by the English in 1658. Shawnee and Susquehannock Indians once occupied the land, and memorials to both are located within the town.

The Upper Bay Museum, housed on the grounds of the North East Community Park, features an extensive collection of hunting and fishing memorabilia. Other parks in the area include Herring Snatchers Park, a popular fishing spot, and Elk Neck State Park, encompassing 2,370 acres of walking trails, beach, boat launch, and camping facilities.

North East's iconic Main Street offers shoppers antique stores, collectibles, jewelry, and clothing stores. Along this walkable stretch of the street are coffee shops, bakeries, ice cream shops, and charcuterie stores.

Some of the best restaurant choices in North East are found along Main Street and include Woody's Crab House, Snatcher's Creekside, Steak and Main, and Woody's Tacos and Tequila. If you prefer waterfront dining, check out the Nauti Goose, offering nightly entertainment and views of the North East River.

Berlin

Historic downtown Berlin, Maryland, featuring old brick buildings and narrow streets lined with small shops for tourists.
Historic downtown Berlin, Maryland. Editorial credit: Kosoff / Shutterstock.com

With just over 5,000 people, Berlin is a small town in Worcester County that is steeped in history. Once home to the Assateague and Pocomoke Indians, Berlin was part of the Burley Plantation, a 300-acre land grant that dates to 1677. The town was officially founded in 1868 and became a popular spot for fishers and hunters as well as those who were on their way to the resort town of Ocean City.

Forty-seven structures in Berlin are on the National Register of Historic Places and represent architecture from the Federal, Victorian, and 20th-century periods. An easy walk through town provides visitors with spectacular views of these buildings. The town's iconic Main Street was featured in the films "Runaway Bride" and "Tuck Everlasting." Berlin's Main Street benefits from the Maryland Main Street Program, which helped improve the street's image, economy, design, and appearance.

Ocean Downs Casino features live and simulcast harness racing, dining, and slot machines, for those who want to try their luck. The casino opened in 1949 at a cost of $650,000, and today is owned by Churchill Downs, Inc.

The Sterling Tavern on Main Street offers patrons pub food and an easy atmosphere. The Globe, on Broad Street, is a former theater turned eatery and lounge offering seafood, drinks, and live music.

Cumberland

A church in Cumberland, Maryland, set against the backdrop of the city’s historic buildings and surrounding hills.
Aerial view of a church in Cumberland and the surrounding town of Maryland.

Cumberland's population is just under 20,000 people. The western terminus of the Chesapeake and Ohio (C&O) Canal, Cumberland was the starting point of the first National Road, known as Route 40 or National Highway today. Tucked away in the Allegheny mountains, Cumberland has been revitalized into an arts community but has retained its small-town ambiance.

The Western Maryland Scenic Railroad offers train trips through the Allegheny mountains and departs from Cumberland. This three-hour round-trip provides riders with spectacular mountain views from Cumberland to Frostburg and is not to be missed.

Cumberland's Arts and Entertainment District is one of 28 districts designated by the Maryland State Arts Council to promote community involvement, tourism, and revitalization. Theatre, art galleries, dining, cafes, and other attractions can be found throughout the district.

Popular restaurants in Cumberland include the Baltimore Street Grill, featuring casual dining; City Lights, with Maryland seafood on the menu; Ristorante Ottaviani, a Tuscan Italian restaurant; and The Crabby Pig, a barbeque joint.

Slow Down and Smell the Roses in Maryland's Towns

The next time you are looking for a quieter, more serene getaway in Maryland, consider visiting one of these nine slower-paced towns. Whether you seek the mountain splendor of Oakland and Cumberland or the coastal serenity of Berlin and Havre de Grace, these towns embody the idea of the Maryland motto, "Strong Deeds, Gentle Words." Maryland offers visitors many opportunities to slow down, smell the roses, meet new people, and make the most of life.

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