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Maryland has many unique attractions to explore within its metropolises and capital cities, but seeking a quiet trip to a small town can be equally as blissful in the state in its small towns, particularly during fall. The delights of small towns in Maryland include the historic city of Snow Hill, and calm towns with populations of just over 100, such as Hillsboro. Adventurous rides in the waters, kayaking, boating, and cruising in the Potomac River of Brunswick and Pocomoke River of Snow Hill are open to thrill seekers. Outdoor fun reaches new levels with hiking on scenic trails, revealing the glory of red and yellow vegetation of the changing seasons in Cunningham Falls State Park, Pocomoke State Forest, and Brunswick Crossing Valley Trail South. When seeking a tranquil fall getaway, these least crowded towns in Maryland are the best places to catch fall foliage.

Thurmont

Thurmont is a small town with a population of just over 6,000 located in Frederick County. It has excellent attractions perfect for fall viewing, including parks and natural preserves such as the Community Park and Catoctin Wildlife Preserve. Nature lovers can watch the picturesque waterfall surrounded by vibrant orange leaves at Cunningham Falls State Park. Hikers may travel through the Cliff Trail Loop and Cat Rock trails here, surrounded by lush trees with tinted leaves. The Catoctin Mountain Park also unleashes adventure in the fall through its deep forested trails, beautiful views of the Monocacy Valley, and pristine waters enough for various recreational activities. The Catoctin Wildlife Preserve provides outdoor lovers with nature and wildlife all while viewing the vistas atop the Catoctin Mountains. The town has a very good commuting facility, making it hassle-free for visitors to go almost anywhere by bus or train. So, don’t wait long as the best time to visit this town is in late September and early October when fall colors peak before winter comes knocking. 

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Leaving the noise of crowded cities to venture to small towns like Crisfield is a great choice this fall, whose population is less than 3,000. Known as the ‘Seafood Capital of the º£½ÇÉçÇø,’ Crisfield gives a soothing feeling as it is a gateway to the beautiful Smith and Tangier Islands, whose landscape reflects the bright colors of red leaves. 

The Janes Island State Park has 30 miles of water trails, cabins, campsites, and walking trails leading into the water, mirroring the beaming color of autumn. It is also an excellent place to birdwatch as various species romp the area. The Somers Cove Marina offers a trip into the best cruising, fishing, and sailing opportunities on the Chesapeake Bay while basking in the autumn air. Crisfield's seafood heritage is a vital part of the town, showcased in their food at restaurants such as The Crab Place, Southern Connection Seafood, and Linton's Crab House & Seafood Carry-Out. The availability of restaurants may be limited and it is suggested to make reservations, as changes can be made in their operation with time. The ideal time to visit Crisfield is late September and early October. 

Snow Hill

Snow Hill is in Worcester County, Maryland, with a population of approximately 2,000 people, offering tranquility amidst the bustle of autumn. This small town has lively events despite its size, located on the Eastern shore of the Pocomoke River with a living history. It was founded in 1686 and made the royal port by Englishmen (William and Mary). Fall adventures here can start with paddling on the dark waters of the Pocomoke River or Nassawango Creek, with surrounding tinted foliage on a calm morning. The Pocomoke area also offers bird watching with species like hummingbirds, raptors, and warblers. Wildlife and plants change due to season, especially the bald cypress plant. The Pocomoke State Forest in early October provides a great experience to get closer to the autumn hue due to the trails surrounded by transitioning leaves, and an opportunity to hike through the woods to explore more. Iconic stories of this little town in its historic sites are told at places such as the Furnace Town Living Heritage Museum. The best time to see birds here is in the late mornings and afternoons during their migration. 

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As the county seat of St. Mary's County for almost three centuries, Leonardtown is a small town with a big feel, housing various beautiful attractions. It has rarely seen much population growth in the past five years. The Patuxent Adventure Center has a water trail that leads to the wharf, gently flanked by colored vegetation, making this a beautiful option to experience fall foliage. There is also paddling, boating, and kayaking on Breton Bay. An unforgettable cruise ride with the wharf journeys from Breton Bay to St. Clements Island, highlighting the tranquility of the waters. Award-winning wine at Port of Leonardtown is found in a lush green park that promises other activities with its walking trails, kayak launch, and winery. Golfers can enjoy the natural atmosphere at Breton Bay Golf Course & Country Club, laden with other options like tennis clubs, restaurants, and aquatic courts. A tour through history in the awe-inspiring scenery of historical sites such as the Old Jail Museum and Leonardtown Visitors Center accentuates the town’s culture. It's best to explore the area with a tour guide to familiarize yourself with the town. It's even more wholesome to experience these places with a company or a partner to absorb its history together.

Brunswick

Brunswick has a population of over 8,000 and is located on the north bank of the Potomac River in Maryland. With the Brunswick Heritage Museum and parks and natural areas such as City Park East Potomac Street and Kim Weddle Park that exude the glory of the season, there is much to take in and discover during the fall. 

A popular time to visit is when fall peaks from late September to October. Walking around Brunswick City Park or biking through the tree-lined paths allows room to enjoy the atmosphere. The park also has playgrounds for kids and is a good place for a dog walk. The park is filled with gorgeous natural scenery, various plant species on display, and hiking trails like Brunswick Nature Trail and Long Leaf Trail. More trails with abundant vegetation give you a full peek into the change of forms and colors of plants that are at Brunswick Crossing Valley Trail South and Rivers Edge Trails. The town's heritage is enveloped in the Brunswick Heritage Museum, exhibiting its past tales and culture. Brunswick cooks up fall festivals every year so plan for a trip around late September to October, for residents and visitors, so peek into their calendar to plan your trip accordingly.

Berlin

Berlin is a beautiful town with a thriving community ranging over 5,000 in population. It is within the Salisbury, Maryland-Delaware Metropolitan Statistical Area. The city has a well-grounded arts and entertainment scene with many beautiful places to see in the fall, including parks, historic sites, and shops. It was founded in the 1790s but was incorporated after the Civil War in 1868. It grew into a famous spot for tourists who sought hunting and fishing opportunities on the Eastern Shore. The Assateague State Park on Assateague Island presents a beautiful view of the water from the shores. It's also a perfect place for equestrians, as the place offers horseback riding in the golden fields of the park. Also, museums and historic sites with peculiar stories of the town's history make exploring the suburbs familiar with the Mermaid Museum and Calvin B. Taylor House Museum. Playing golf is one of the best ways to soak in the season at the Rum Pointe Seaside Golf Links for an exclusive time with the sport. Berlin's new attraction, Tracks and Yaks, is a unique, fun activity with railbiking that is rising in popularity. The best time to visit here is in the peak of fall in October.

Hampstead

Hampstead promises the season's warmth with its cozy feeling and small population. Tourist’s favorite spots are found by touring the different attractions in this small town. Dates with nature at Prettyboy Reservoir Park tease beautiful vistas of natural scenery featuring red leaves and wildlife while hiking through the trails. Animal species such as Wild turkeys, Pickerel frogs, and Northern Red-bellied cooters are found around the area. Leister Park also has impressive views of autumn foliage. The Deep Run Farm Stand supplies the best produce for the season, including giant pumpkins and other vegetables. Hampstead's fall events include the Hampstead Fall Fest, featuring entertainment and culture on display. From Baltimore, there are four ways to get to Hampstead: subway, bus, taxi, or car, but the fastest route is by taxi. So, pack your bags as there’s no bad time to visit Hampstead. However, Late August to November are the best times to visit in the fall

Chestertown

Chestertown is a beautiful small town in Kent County, providing a combination of art, Maritime history, and culture for fall visitors. The city is prevalent with parks and locations that exude a fall feeling and fun. The town was founded in 1706 and was used as a major port of entry during colonial times. It has become a beautiful city with brick sidewalks and unique antique shops. The best time to visit is during warm weather activities that end in late September, and fall Exploration of the best recreational activity while dousing in the refreshing autumn air is at Ajax Park, Fountain Park, Gateway Park, Wilmer Park, and Louisa d'Andelot Carpenter Park. The Chestertown Historic District reveals a brief insight into the town's heritage with the area's unique architectural styles. Collectible antiques and art in antique shops such as Bee Crafty Collectibles and Poor Richards of Chestertown are open to all shoppers. Traveling to this town from September to November is more budget-friendly as the other times of the year are more hectic here. 

Mount Airy

Mount Airy is within the Washington and Baltimore Metropolitan Area but maintains its uniqueness in its urban offerings, including a touch of wildlife and adventure at the peak of the fall season. Wine and beer available with the crisp autumn air set the fall tone in this small town with vineyards and wineries. They have beautiful environments classified by natural vegetation, giving into the seasonal change in colors, such as Black Ankle Vineyards, Linganore Winecellars, and Elk Run Vineyards. The Gaver farm has loads of richly-grown produce this season, particularly pumpkins. The farm also organizes weekday hayrides and free hayrides on the weekends for visitors. Wildlife and natural phenomena are explored at Audrey Carroll Audubon Sanctuary, watching bird species migrate, including Raptors, Purple Finch, and Lincoln Schedules of each place are available for trip planning. A great time to visit is when the downtown area in October leaves room for participation in the town's annual Oktoberfest celebration.

Hillsboro

Hillsboro's small-town charm and fantastic locations for perfect fall getaways keep visitors trooping, despite having only over 100 population. The best time to visit is late September to October One of its prime highlights is the Hillsboro Town Park and Playground, featuring refreshing walks in the fast-paced walking trail amidst the radiant foliage and fun activities such as camping and picnicking. Trips to the nearby Adkins Arboretum in Tuckahoe State Park consist of a 400-acre native garden with various plant species from shrubs to wildflowers. The town also offers boat ramps near the bridge between Hillsboro and Queen Anne, where there are boats, kayaks, and paddles in the clean water. The Movie Nights in the Park are perfect for a calm evening before settling in the town. Every fall, the annual yard sale with its neighboring town, Queen Anne, lets shoppers purchase various items for keepsake.

While these towns are relatively small in population, they offer a glimpse into the best experiences, away from the loud bustling of large cities in the crisp air of autumn. From the beautiful, natural feel of the pristine Potomac River in Snow Hill reflecting fall hues, to exploring lush forests beaming in the radiant season at Catoctin Mountain Park in Thurmont. These least populated towns strive to give visitors the best fall experiences. Trips to picturesque-themed architectural buildings in Chestertown and the elegant structure of old-standing historic buildings in Leonardtown and Thurmont supply history buffs with the culture of the towns. Pumpkin picking and other activities to be pursued are in Mount Airy's agricultural offerings at Gaver farm, with nicely grown produce and weekly hayrides. With numerous outdoor activities in these small towns, the autumn exploration is endless.