Aerial view of Saint Michaels, Maryland.

These 7 Towns In Maryland Feel Like Home

The definition of home varies from person to person. Some may find solace in a rural retreat, whereas others feel peace along the shoreline or in a historic small town. Every corner in Maryland feels like a dream come true with a welcoming community and a peaceful haven. Wander around St. Michaels, a serene waterfront marvel with a lighthouse showcasing a bygone era. Head to Grantsville or Boonsboro for a taste of rural Maryland. Discover the state's food scene in Berlin and then walk off the meal at Assateague State Park, where the wild horses trot about. The state offers unlimited opportunities for a heartwarming adventure.

Chestertown

Aerial view of Chestertown on the Chesapeake Bay in Maryland
Aerial view of Chestertown on the Chesapeake Bay in Maryland.

With roots dating back to 1706, Chestertown is a historic college town steeped in history. Hugged by the tranquil shores of the Chester River, the landscape unfolds with striking views. Stroll along the dreamlike waterfront or head downtown where the brick-paved sidewalks are lined with art galleries, cozy cafes, and local boutiques. Spend an afternoon wandering MASSONIART with ever-changing exhibits to keep things fresh. The diverse range of works is intriguing to all tastes. Past exhibitions include Marcy Dunn Ramsey's Balance, art by Joe Karlik, and Marc Castelli's Brutal Elegance of Log Canoes. Afterwards, rejuvenate with a cup of coffee at Play It Again Sam, a charming cafe just a short walk from the gallery. Get comfortable with a matcha latte, iced mocha, while indulging in a delectable salad or sandwich.

Visit Chestertown in May for the annual Chestertown Tea Party Festival, taking place in the historic district and along the Chester River. From a street party to a colonial parade, craft beer tasting, and even a historical reenactment, the event perfectly blends modern times with Maryland's past.

Berlin

Historic downtown of Berlin, Maryland
Historic downtown of Berlin, Maryland. Image credit: Kosoff / Shutterstock.com.

Berlin is one of Maryland's best-kept secrets. Due to its proximity to the Atlantic Ocean and its bustling downtown area, Berlin boasts a thriving dining scene. Try seafood fresh from the source at the Atlantic Hotel Bistro Bar, also known as the Drummer's Cafe. Indulge in a romantic dinner at the heart of Berlin's historic district. Savor a pan-seared salmon, broiled cod, stuffed shrimp, or the seafood grand slam. Raise a glass at the beloved Burley Oak Brewing Company, where exceptional brews highlight Maryland's finest. From the Bulldog English Ale to Tiramisu Pastry Stout, Adventure IPA, and Cashmere Cowboy Double IPA, there is something for every palate. Pair it with some California-style street food from the kitchen and call it a day well spent in Berlin.

Equal parts unique and otherworldly, watch the wild horses roam at Assateague State Park, the state's only oceanfront park. Aside from seeing these majestic creatures wander, the area is remarkable for getting active. Head out in the crashing waves for an incredible surf session, glide through the waters by swimming, or grab a fishing rod and find a fresh catch. Make it even more memorable by renting a campsite and sleeping under the stars.

Boonsboro

Aerial view of Boonsboro, Maryland, from South Mountain
Aerial view of Boonsboro, Maryland, from South Mountain.

Located along the iconic Appalachian Trail, Boonsboro is a beautiful rural town in Maryland that feels like home. Surrounded by gorgeous farmlands, Boonsboro is a quintessential American small town with a close-knit community, Civil War ties, and olden-day architecture. Support local farmers and pick up some fresh produce from Cronise Market Place. Grab some summer berries, springtime tomatoes, or fall apples to craft up something delicious in the kitchen with a taste of Maryland. Stay awhile in peaceful Boonsboro by booking a few nights at the Inn BoonsBoro. Originally built in the 1790s, the accommodation is an exquisite blend of luxurious elegance and a comforting bed and breakfast. Many guests praise the convenient location and say it's one of the best lodging options in town.

Join the locals for the annual Boonesborough Days, a September extravaganza. Mingle in Shafer Park and check out exhibitors, Civil War displays, and rows of vendors. From crafts to candles, skincare, flowers, crochet items, and pet accessories, it makes for the perfect Maryland souvenir.

Treat the kids and cool down with some ice cream at Potomac Street Creamery. Satisfy sweet tooths all around with this nostalgic treat. With classic flavors like Cookie Dough, Mint Chip, Black Cherry, Butter Pecan, and Chocolate, there is a little something for everyone. Add some sprinkles on top and watch the whole family smile from ear to ear.

Mount Airy

Downtown Mount Airy, Maryland
Downtown Mount Airy, Maryland. Image credit: R. London via Wikimedia Commons.
Surrounded by a hilly terrain and a forested landscape, Mount Airy is a renowned railroad town with friendly locals. The best way to take a deep dive into a slice of Maryland's heritage is by checking out the Mount Airy Museum. Conveniently located in the historic Mount Airy Station, the museum features engaging exhibits on the town’s school system, the Robert Garrett Sanatorium, and local industries like canning and sewing. One of the most intriguing features is an interactive train diorama that brings the region’s rail history to life.
Maryland is a flawless masterpiece during the autumn months, when the state turns into a canvas of warm reds, oranges, and golds. Fall in Mount Airy means a well-needed trip to Gaver Farm. Running from the end of August until the beginning of November, Fall Fun Fest is pure perfection. Get lost in the corn maze, say hello to the barn animals, glide on the bee zipline, and race on the pedal karts. Stroll through the orchard and fill up a bag of juicy apples. Afterwards, head to the pumpkin patch for gourds, winter squash, and a future carving project. Hop on the hayride after all the fun to cap off an adventurous fall day.

Springtime brings the Love Your Park Week to Mount Airy. Various centers and parks around the town offer activities for all ages. Whether it's storytime at the library, a nature walk, an introduction to mountain biking, or a rock skipping contest, the weeklong calendar is a terrific way to embrace the coming of the warmer months.

St. Michaels

The St. Michaels Harbor in historic Saint Michaels, Maryland.
The St. Michaels Harbor in historic Saint Michaels, Maryland.

With magazine-worthy sunsets and marina views for miles, St. Michaels is a coastal paradise on Chesapeake Bay. Bring a camera for the photoshoot of a lifetime at the 1879 Hooper Strait Lighthouse. The 19th-century lighthouse has served as a notable St. Michaels landmark since 1879. Head inside and learn about the ins and outs of being a lightkeeper. Those wishing to be on the waters themselves should book a cruise through Patriot Cruises. Book a group tour or embark on a private charter and coast on the Miles River. Bask in panoramic views of St. Michaels and the surrounding area while passing by historic mansions.

Gather some friends and get ready to wine and dine in Maryland. Book a tasting at St. Michael's Winery and sample some specialties. From time to time, sangria and mulled wine are on the menu. Be sure to pick up a bottle of your new favourite at the shop. Be enchanted by the extensive wine list. Choose from dry wines such as Sparkling Vidal Blanc and Maryland Chardonnay, or try a sweet wine like Bubbly Black, Gollywobbler Peach, or Chocolate Zin. Nothing says on the coast quite like some waterfront dining. Soak in the views at The Crab Claw Restaurant and feast on Maryland Crab Soup, Cherrystone Clams, or Chesapeake Bay Oysters.

Grantsville

The old stone Casselman Bridge at Casselman State Park, Grantsville, Maryland.
The old stone Casselman Bridge at Casselman State Park, Grantsville, Maryland.

Grantsville is a hidden treasure in rural Maryland. Embraced by rolling hills and dense forests, the secluded small town is thriving with Amish and Mennonite influences. Take home a previously loved item from Blue Moon Antiques. Turn heads with a vintage outfit paired with antique jewelry. Decorate back home with a carpet, pottery, or porcelain piece for a one-of-a-kind souvenir. Savor the quiet country life by staying a few nights at The Casselman Inn, a historic showpiece standing proud since 1842. Impressive from every angle, the guestrooms are comforting and elegant with timeless touches. Wake up to a complimentary breakfast featuring a variety of hearty and lighter options. Feel right at home with buttermilk pancakes, yogurt, eggs with toast, oatmeal, or biscuits and gravy.

Step into a fairytale at Spruce Forest Artisan Village, a rare find in Grantsville. This cherished Maryland attraction features handmade arts and crafts in restored log buildings. From basket making to stained glass art, handcrafted soaps, and teddy bears, the selection of works is astonishing. For a more hands-on approach, take part in one of the workshops. Become a pro at fabric art, colored pencils, watercolor, or collages while learning from the best.

Havre de Grace

Distant lighthouse in Havre De Grace, Maryland
Distant lighthouse in Havre De Grace, Maryland.

Founded in 1782, Havre de Grace is brimming with some of Maryland's oldest roots. Right along the Susquehanna River, the port city boasts sweeping vistas, an old-world downtown, and a cozy overall vibe. Take a sunset or sunrise stroll down the Havre de Grace Promenade. Watch the ducks splash in the sparkling waters while breathing in that fresh, salty air. Watch history unfold by taking a trip to the Concord Point Lighthouse, the oldest accessible lighthouse in the state. Check out the Keeper's Dwelling, which remains true to its 1884 era. Book a tour of the interior and climb to the top for panoramic views of Havre de Grace's natural beauty.

Putt the day away at Bulle Rock Golf Course, known for being one of the best golf courses in Maryland. Designed by Pete Dye, the course is a top choice by Golf Digest. With endless views of lush greenery, ponds, and hills, the 235-acre course is heaven for golf enthusiasts. Fuel up after the game at the Gourmet Pub & Grill. The menu offers an array of choices from classic favourites like Shrimp Scampi to finer feasts like a Coffee Rubbed New York Strip Steak.

Feel Right at Home in Welcoming Maryland

Head to the Mid-Atlantic region for a cozy stay in welcoming Maryland. Check out the Farmer's Market in rural Boonsboro for fresh produce and a chat with friendly neighborhood farmers. Fill up on some of the best fresh seafood in Berlin. Be the main character in a storybook by strolling around the enchanting Spruce Forest Artisan Village, or by venturing down the Havre de Grace Promenade. Head to Mount Airy for some fall fun at Gaver Farm and to learn about Maryland's enticing railroad history at the local museum. The state is an alluring combination of friendly residents, compelling attractions, indulgent dining, and endless scenery.

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