Aerial view of a bridge at Prettyboy Reservoir Park with fall colors, Hampstead, Maryland.

7 Small Towns In Maryland That Come Alive In The Fall

Fall is an ideal time for a getaway in Maryland to experience the best of nature with transitioning leaves, the crisp air, and accompanying festivals. The small towns in Maryland offer leaf-peeping opportunities, like in the Catoctin Mountains and Wildlife Preserve. Walk on the tree-lined streets of Bel Air and pick pumpkins in the pumpkin patches of Chesapeake City.

Find the best spots to be enchanted by fall foliage in these charming small towns, including Berlin, Chesapeake City, Oakland, and Thurmont. With peculiar experiences in each town, be ready to discover the various park activities in Havre de Grace, fish in the river at Cunningham Falls State Park, learn the Chesapeake City's heritage at C&D Canal Museum, or take part in Oakland's Autumn Glory Festival. Find the best Maryland small towns that come alive in the fall.

Havre de Grace

Autumn color along the promenade at Concord Point, in Havre de Grace, Maryland.
Fall colors along the promenade at Concord Point in Havre de Grace, Maryland.

Havre de Grace is a picturesque small town in Harford County, offering a host of unique experiences to visitors who wish to watch the changing of colors in the fall. The town is home to a variety of parks and trails that showcase nature and wildlife, like Concord Point Park, a waterfront park overlooking the Susquehanna River, which allows you to relish the freshwater feel and the transitioning leaves. Nearby Susquehanna State Park is also a perfect destination for nature lovers, with several recreational opportunities like hiking, biking, and picnicking.

Take a therapeutic walk on the Havre de Grace Promenade (Boardwalk) and revel in the crisp air and picturesque fall view. There are also historical sites and museums, like the Swan Harbor Farm and Decoy Museum. Lastly, the town hosts fall festivals such as the Fall Harvest Festival yearly in the Steppingstone Farm Museum, where visitors can experience music performances, history, and heritage.

Bel Air

Bynum Run Creek in Bel Air, Maryland in the fall.
Bynum Run Creek in Bel Air, Maryland.

Located in Northern Maryland, Bel Air is a small town with the best fall exploration opportunities for fall lovers, from tree-lined sidewalks and a blend of old and new architecture to historic buildings and parks. Enjoy a leisure walk on the Ma & Pa Heritage Trail Boardwalk, stretching over six miles, or hike through the fall paths while observing the changing season and beautiful views.

The town's history is preserved in historical sites and art venues like the "House and the Healing Garden'' mural in the Kaufman Cancer Center. Rockfield Park spans 51 acres with gardens and trails that showcase fall colors and provide leisure time. Check out the Memorial Tree Grove at Shamrock Park, consisting of trees and a memorial dedicated to Bel Air Residents that offer an excellent view during fall and a peek into history. 


Vibrant autumn photo taken in Swallow Falls state park in western maryland
Autumn colors at Swallow Falls State Park, near Oakland, Maryland.

As a small town with an idyllic setting, Oakland is tucked between mountains in Southern Garrett County near the Deep Creek Lake. There are many reasons to believe this town is the perfect fall destination in Maryland; from scenic mountain parks and wildlife adapting to fall leaves, like the Swallow Falls State Park and Bradford Park, to a vibrant art scene in the Oakland arts & entertainment district. Engage in park activities at Deep Creek Lake State Park overlooking the Deep Creek Lake and flanked by fall trees.

Take a walk or bike on the Oakland Heritage Trail or 88 Bridge walking/biking trail to observe the wonders of the changing season, red leaves, and refreshing air. While here, travel through time at the Garrett County Museum of Transportation and Oakland B&O Railroad Museum. Take part in the town's annual Autumn Glory Festival, celebrating fall foliage with several musical performances and art for visitors. 


Thurmont, Maryland, the visitor center for Catoctin Mountain Park on an autumn afternoon with the American flag.
The visitor center for Catoctin Mountain Park on an autumn afternoon, Thurmont, Maryland. Image credit Liz Albro Photography via Shutterstock

Thurmont is a small town, 10 miles from the Pennsylvania border, with a picture-perfect view at Catoctin Mountain Park, with space for everyone to explore. You can hike or cycle through the Catoctin Mountains or learn about wildlife, observing about 600 wildlife animals at the Catoctin Wildlife Preserve and Zoo.

Cunningham Falls State Park, which has the largest cascading waterfalls in Maryland, spans nearly 43 acres and is known for its picturesque landscape that shines even better in fall. The lake provides recreational activities, including fishing, hiking, hunting, and camping. Visit one of Thurmont's orchards, like the Pryors Orchard or the Catoctin Mountain Orchard, which allows visitors to pick fruits while soaking in the classic fall foliage in the small town.

Chesapeake City

Chesapeake City Bridge at Sunset, Maryland USA, Chesapeake City, Maryland
Chesapeake City Bridge at sunset, Chesapeake City, Maryland.

This enchanting small town is registered on the National Register of Historic Places for its notable landmarks like the C&D Canal Museum, excellent 19th-century architecture, and historic sites like the Chesapeake City Historic District. The town also rests at the northern end of the Chesapeake Bay, the largest estuary in the United States. It has a working commercial canal and is laden with abundant natural paths that change with the season.

Chesapeake City offers visitors a relaxing walk or drive through the Ben Cardin Recreational Trail or Chesapeake Wine Trails — a taste of fun and wine. You can spend all day wowing about fall foliage or discover arts, antiques, trendy wear, and ornaments in these high-spirited downtown shops like Belle on Bohemia and Old Gray Mare and Chick's.


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

Berlin is in Worcester County and is a part of the Salisbury, Maryland-Delaware Metropolitan Statistical Area. It is most known for its lively main street and relaxing outdoor experience. The town showcases nature in the fall with its newest attraction, Tracks and Yaks, offering tours like the Ironshire Express, taking visitors through historic farmlands and coastal forests, and Queponco excursion for cyclists through a 13-mile excursion along coastal forests. Another popular attraction is the nearby Assateague Island National Seashore.

You can experience fall events such as Berlin Fall Cruisers, which showcases cruisers and cars in the downtown main street. There is also the Berlin Farmers Market featuring various foods from various bakers, food cultivators, seafood, and more. When you are done, take a historic break to The Mermaid Museum, showcasing the mythical creature. You can also witness the beauty of art at Worcester County Arts Council and the Henry Fine Arts Gallery. Lastly, have a relaxing moment with your family surrounded by the changed color of leaves in any of Berlin's four parks: Stephen Decatur Park, William Henry Park, John Howard Burbage Park, and Heron Park.


Aerial of Pretty Boy Reservoir Dam in Hampstead, Maryland during Fall
Overlooking Pretty Boy Reservoir Dam near Hampstead, Maryland, in the fall.

First called Spring Garden, Hampstead is in Carroll County, home to pristine greenery and agriculture. You can revel in the glory of fall while engaging in adventurous activities like biking and swimming in Leister Park. Experience a unique getaway at the Prettyboy Reservoir Park, the ideal place to watch the beauty of red leaves and different species of birds.

The dam's trail is a long walk across 2.6 miles, but it is worth it for those who want to take a relaxing stroll while enjoying the best the season offers. You can find freshly grown produce while you witness fall colors in farms like the Deep Run Farm Stand and experience the farming community. Take part in the Hampstead Fall Fest, featuring arts, agriculture, and entertainment.

Winter is fast approaching, so there is no time to sit around; these small Maryland towns will spur you off your couch and get you in an exploring mode this fall. Take your time to discover agriculture in farms and orchards while soaking in fall foliage and grabbing souvenirs at Steppingstone Farm Museum in Havre de Grace and the Deep Run Farm at Hampstead. As long as you are ready, these towns will welcome you warmly, so pack your bags and get exploring this fall.

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