Store decorated for Halloween on Talbot Street, St. Michaels, Maryland. Image credit Albert Pego via Shutterstock

11 Small Town Getaways In Maryland Perfect For Families

There are many reasons to visit Maryland, especially if you’re planning a family vacation. Its charming small towns present the perfect setting to spend quality time with loved ones, away from the chaos in the big cities. The state boasts beautiful natural landscapes, unique cultural attractions, friendly communities, and fun outdoor adventures, ensuring there is something to keep everyone entertained regardless of age or preference. From lively downtown streets to hiking along picturesque trails to sleeping under the stars in primitive campsites, the stage is set for an unforgettable family experience. For lasting memories, these small-town getaways in Maryland are tailored to the ideal family holiday.

McHenry

People standing outside the lodge at the Wisp Ski Resort located in McHenry, Maryland
The Wisp Ski Resort in McHenry, Maryland. Image credit Wirestock Creators via Shutterstock

This idyllic small town, tucked away on the shores of Deep Creek Lake, delights with stunning natural scenery and a raft of kid-friendly adventures. The Fork Run Recreation Area is an excellent spot to explore nature, surrounded by a thick, lush wilderness and brimming with flora and fauna. McHenry also holds a special place in America’s history. James McHenry, who established the town in the 1700s, was among the original signatories of the United States Constitution.

However, what makes the town an ideal option is its long list of fun, family-friendly venues. The Deep Creek Fun Zone guarantees day-long, unadulterated entertainment for the whole family; it has an arcade, a mini-golf course, go-karts, and bumper boats. The same goes for the Monkey Business Adventure Park, which thrills with adrenaline-filled adventures like zipline. Meanwhile, Wisp Resort is the perfect lodging option for families in the town, offering remarkable skiing opportunities.

St. Michael’s

Shops and stores in St Michaels, Maryland, along the town's main street.
St Michaels, Maryland, along the town's main street. Image credit George Sheldon via Shutterstock.com

St. Michael’s is a great summer vacation spot for families looking to enjoy Maryland’s beautiful warm weather. Its location on the Chesapeake Bay ensures gorgeous water views, and Patriot Cruises offers an opportunity for the family to enjoy a laid-back trip on the bay, soaking in the spectacular natural scenery that defines the quaint town. St. Michael’s is also known for its rich maritime heritage, which you can experience at the Chesapeake Bay Maritime Museum by browsing unique artifacts, including historic bay vessels like the Edna E. Lockwood.

The town offers numerous family entertainment options, but the highlight is renting a canoe or kayak from Shore Pedal & Paddle for fun on the water. Meanwhile, going souvenir hunting in Antiques On Talbot is an excellent way to pass the time surrounded by loved ones.

Solomons

Dock and water at sunset in Solomons Island, Maryland.
Waterfront in Solomons Island, Maryland.

Solomons Island, a charming waterfront town on the Chesapeake Bay, is known for its boating culture and bustling seafood scenery. Walking along its famous boardwalk presents a snapshot of the stunning scenery in the city, including unprecedented vistas of the Patuxent River. What makes Solomons such a unique destination is its remarkable biodiversity, which features thousands of plants and animal species and vibrant marine life.

One of the best places to take the family is the Annmarie Sculpture Garden & Arts Center. This impressive facility mixes the love for the arts and nature to deliver an unforgettable experience. Meanwhile, booking a tour with Cruisin Tikis Solomons Island allows you to experience one of the best pastimes in the town. Finally, a trip to the island won’t be complete without sampling the sumptuous Chesapeake Bay cuisine. The Lighthouse Restaurant & Dockbar is where you can take the family to savor tasty seafood and steaks.

Rock Hall

Two people sitting by the waterfront in Rock Hall, Maryland with two bikes.
Sitting by the waterfront in Rock Hall, Maryland.

Rock Hall is another cute waterfront location with a rich heritage dating back to the colonial era when it served as a shipping hub for the tobacco, seafood, and agriculture industries. Today, it continues to charm visitors with unique natural attractions, including the Eastern Neck National Wildlife Refuge, teeming with outdoor opportunities like wildlife viewing, hiking, fishing, and hunting. What makes Rock Hall unique is that it is directly located along the National Chesapeake Scenic Byway, offering a starting point for one of the most picturesque drives your family can have in the state.

Among the top attractions in the town is Ferry Park, a gorgeous outdoor space with a beach and gazebo. With generous amenities like barbecue stands, picnic tables, and pavilions, you can plan a fun day out with loved ones against the backdrop of the magnificent Chesapeake Bay. And when the kids get ravenous, they can fill up at the Blue Heron Oyster House & Inn for a taste of the local delicacies.

Fulton

Overlooking the town and Maple Lawn water tower in Fulton, Maryland.
Maple Lawn water tower in Fulton, Maryland.

Fulton’s modest population of just over 4,000 residents leaves enough room for visitors to enjoy its quaint natural scenery, which you can experience at Sunflowers of Lisbon at Maple Lawn. Fulton is also a mini gastronomic mecca, boasting various restaurants specializing in diverse cuisines. The best way to prepare your family for the adventures ahead is to get them started with a wholesome breakfast at the Decadent café and bakery.

Afterward, you can explore the town’s top family-friendly adventures, such as joining the locals at the Farmer's Market At Maple Lawn to shop for farm-fresh produce. Alternatively, your kids will find it fascinating watching free-range turkeys going about their business at the Sho Nuff Turkey Farm. Tourists take advantage of the warm-weather activities in Fulton by scheduling visits between June and September.

Snow Hill

The Pocomoke River at Snow Hill, Maryland.
The Pocomoke River at Snow Hill, Maryland. Image credit Acroterion, CC BY-SA 4.0, via Wikimedia Commons

Snow Hill is a unique town all about fun and hosts exciting adventures throughout the year. From shopping to kayaking and trekking, there’s something to intrigue everyone in the family. If you love nature, the town boasts a long list of charming natural spaces, including the Pocomoke River State Park, where outdoor adventures such as hiking, trailing, camping, and boating await. Founded in 1686, the town has a rich legacy dating back to the pre-Revolutionary era, and this is evident from the well-preserved ancient structures in the area.

An excellent spot to witness this living history is the Furnace Town Historic Site inside the Pocomoke Forest, which depicts village life in Snow Hill as it was in the 19th century. To ensure that the kids have the time of their lives, take them on an exciting journey along the river with the Pocomoke River Canoe Company.

Berlin

Wild ponies grazing on marsh vegetation in late winter at Assateague Island National Seashore on the Atlantic Ocean in Berlin, Maryland.
Assateague Island National Seashore on the Atlantic Ocean in Berlin, Maryland.

Voted "America’s Coolest Small Town," Berlin has genuinely earned its moniker; shielded from rowdy crowds and bustling with hidden gems to discover, the town promises an unforgettable family adventure. Nature lovers gravitate towards Assateague State Park, which has the distinction of being the only oceanfront park in the state. Berlin is also famous for having one of the liveliest Main Streets in America, lined with at least 60 shops, restaurants, and art galleries.

While exploring the town, stopping at the amazing Mermaid Museum will surely leave the young ones in awe of the exhibits inside. If not, you can take them to The Dusty Lamb for a cute gift or souvenir they can take back home. Finally, check into the historic Atlantic Hotel for the perfect accommodation experience.

Chesapeake Beach

Looking down the pier in Chesapeake Beach, Maryland.
The pier in Chesapeake Beach, Maryland.

One of the scenic beachside getaways in Maryland to spend time with family is at Chesapeake Beach, a quiet community of about 7,000 filled with water-based adventures. The town’s natural scenery can be absorbed along the 2-mile Chesapeake Beach Rail Trail, surrounded by breathtaking creeks and marshlands. The town is also an excellent escape from the hustle and bustle of the state capital, Annapolis, and the country’s capital, Washington D.C., both of which are about 30 miles away.

Chesapeake Beach boasts an array of kid-friendly venues, and booking a session with DMV Jet Skis guarantees a remarkable experience for the whole family. Meanwhile, Tyler’s Tackle Shop & Crab House is ideal for sampling the state delicacy.

Oakland

Autumn colors at Swallow Falls State Park, near Oakland, Maryland.
Swallow Falls State Park, near Oakland, Maryland.

Not to be confused with the port city on the West Coast, Oakland, Maryland, is a modest and underrated community tucked away in the westernmost portion of the state. Swallow Falls State Park is one of the best places to commune with nature and houses the state’s highest free-falling cascade. Besides admiring the 53-foot natural wonder, the park has plenty of walking trails and campsites, perfect for an outdoor family adventure. Oakland is also home to the Garrett County Historical Museum, full of over 200 years of exhibits about the area.

Kids will fancy visiting the Circle R Ranch, a family-friendly venue with fun adventures like laid-back pony rides, guided trail rides, and hay rides. But for a more contemporary, fun activity, Deep Creek Lake Bowling offers day-long family entertainment, complete with great food and delicious desserts.

Bel Air

Facade of the castle-looking armory in Bel Air, Maryland
Armory in Bel Air, Maryland. Image credit Jerrye & Roy Klotz, MD, CC BY-SA 3.0, via Wikimedia Commons

The seat of Maryland’s Harford County, Bel Air has a little bit of everything to offer, from historical attractions and artistic delights to natural adventures. Hiking along the Ma and Pa Trail is the perfect way to explore the town. This scenic path snakes through woodlands and creeks, placing you in the thick of Bel Air’s backcountry. You can glimpse the town’s history at Hays House Museum, the oldest structure in the region, built in the 18th century. It is a snapshot of what the town looked like during its formative years.

When it’s time for the young ones to play, a trip to the Jurassic Golf & Arcade is a popular stop. This dinosaur-themed venue boasts animated dinosaurs and CGI effects that will excite the children as they perfect their swing on the mini golf course.

North Beach

Boardwalk along with the water and home in North Beach, Maryland.
Boardwalk in North Beach, Maryland.

Another picture-perfect beachside escape in Maryland, North Beach delights with a serene atmosphere and fun water-based adventures. "The Jewel of Chesapeake Bay," as it’s popularly known by the locals, lives up to its moniker with sweeping views of the bay. You can experience this with an easy-going seaside stroll along the North Beach Boardwalk, where kids will love playing at the "shipwreck" sandbar.

Then there’s the town’s famous pastry shop, the bakist, which is the best way to start the day. As adults enjoy a lavender latte or espresso, kids can curb their sweet cravings with chocolate chip cookies and blueberry scones. Another viable attraction for the whole family is the Bayside History Museum, which preserves the cultural and natural history of the North Beach community, as well as the surrounding region.

Sometimes, spending quality time on a laid-back vacation in an isolated destination devoid of the city hustle and bustle is the perfect way to come together as a family. Luckily, the Old Line State was tailor-made for such getaways, thanks to a long list of charming small villages. These small-town getaways in Maryland offer a once-in-a-lifetime family holiday.

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