2025's Towns In Maryland That Come Alive In The Fall
As the summer humidity fades, Maryland transforms. A welcome crispness sharpens the air, and the landscape erupts in a breathtaking blaze of crimson, gold, and amber. This is the season when the state's most charming cities truly shine, swapping lazy lake days for harvest festivals and scenic drives down leaf-canopied roads.
To catch this fleeting show, timing is everything. The color famously starts in the western mountains, with Garrett and Allegany counties seeing their peak from early to mid-October. It then rolls east, lighting up the central region's valleys around late October, before concluding its journey on the Eastern Shore, where its glow often persists until early November. Here are nine towns perfect for your 2025 fall adventure.
Havre de Grace
Havre de Grace offers a late-season show, with its best colors arriving from late October into early November. Its prime spot, where the Susquehanna River meets the Chesapeake Bay, means you can see the brilliant forest reflected on the open water, creating a stunning two-for-one view. A simple walk along the Havre de Grace Promenade is a must. This boardwalk traces the waterfront, offering panoramic views of the fiery foliage across the river and a great spot for watching migratory birds. For a true hike, nearby Susquehanna State Park offers trails like the Susquehanna Ridge Trail, which climbs high above the river for breathtaking vistas of the golden valley. The town also celebrates with outdoor events, including an October Fall Harvest Festival at the Steppingstone Farm Museum and a popular waterfront Havre De Grace Art Show in the parks.
Oakland
For the state's first and most dramatic display, head west to Oakland, where the mountains typically ignite in a blaze of red and gold by mid-October. This area's high elevation means the show starts here, and it is legendary for its scenery. The essential stop is Swallow Falls State Park, where you can hike through ancient forests to see Muddy Creek Falls, Maryland's highest free-falling waterfall, and plunge into a river framed by bright yellow birches and deep red maples. For a different perspective, the quiet lake at Herrington Manor State Park offers a perfect mirror reflection of the surrounding trees.
The entire region celebrates this peak transformation with the famous five-day Autumn Glory Festival. The highlight is the Grand Feature Parade on Saturday, an outdoor community celebration with marching bands and festive floats.
Cumberland
Cumberland is a city set in a stunning natural bowl, surrounded by the ridges of the Appalachian Mountains. The vibrant transformation here is best viewed from mid-October through early November, when the surrounding peaks are ablaze. For an unforgettable panoramic vista, drive to Dan's Rock Overlook, the highest point in the county, to see the sweeping landscape. Another essential stop is Rocky Gap State Park, where the 243-acre Lake Habeeb creates a brilliant blue mirror, perfectly reflecting the golden forests that line its shores. You can walk the easy Lakeside Loop Trail to circle the water and soak in the scenery.
One of the most unique ways to experience the season is on the Western Maryland Scenic Railroad, which offers special "Pumpkin Patch" excursions on weekends in October. This heritage train provides a relaxing ride from the center of Cumberland into the mountains, offering incredible views right from your window. For a more active adventure, Cumberland is the starting point (Mile 0) of the Great Allegheny Passage (GAP) Trail. You can rent a bike and pedal this world-class, nearly level trail as it winds through a spectacular tunnel of golden leaves.
Hampstead
Hampstead is set among the rolling hills and rich agricultural land of Carroll County, which hits its peak around late October. The area's most stunning natural feature is the nearby Prettyboy Reservoir, a massive, protected body of water. As the surrounding forests turn bright yellow and deep red, their reflection on the reservoir's calm surface is a breathtaking sight. You can hike the trails around the reservoir, like the popular Prettyboy Dam Loop, to get right next to the water and under the canopy.
The region's farming heritage is on full display during this time. A short drive away, you can get lost in the enormous "Cornfusion" corn maze in Manchester, a beloved local tradition that also features hayrides and a pumpkin patch. It is open on fall weekends in September and October. For a more relaxed adventure, take a scenic drive on the Carroll Barn Quilt Trail. This self-guided tour winds through picturesque backroads, allowing you to spot large, hand-painted quilt squares mounted on historic barns, all set against the beautiful backdrop of the countryside.
Mt. Airy
Straddling two counties, Mt. Airy sits on a high ridge that catches the full glory of the seasonal transformation, which typically peaks here around late October. The area is defined by its rolling hills and idyllic farmland, making it a perfect destination for classic harvest-time activities. The centerpiece is the massive Gaver Farm Fall Fun Fest, a sprawling celebration that runs through early November. It features over 65 attractions, including a giant seven-acre corn maze, playgrounds, and free hayrides that carry you out to the 12-acre pumpkin patch to find the perfect pumpkin.
Another beautiful escape is the Audrey Carroll Audubon Sanctuary, a 129-acre preserve with trails winding through meadows and forests. It's a serene place for a walk and a prime spot to watch for migrating hawks against the backdrop of the changing trees. You can also explore the outdoors at Wildwood Park.
Thurmont
Known as the "Gateway to the Mountains," Thurmont is the absolute epicenter of the Catoctin Colorfest, one of the largest outdoor craft festivals on the East Coast. Held on the second weekend of October, this massive event floods the town with visitors who come for the hundreds of artisans and the spectacular mountain setting. This celebration perfectly coincides with the area's peak transformation, as the ridges of the Catoctin Mountains turn into a dramatic tapestry of deep reds and bright yellows.
This is a premier hiking destination. Catoctin Mountain Park offers 25 miles of trails, with the hike to Chimney Rock rewarding you with a stunning, rocky lookout over the entire hardwood forest. For an iconic view, head to Cunningham Falls State Park to see Maryland's largest cascading waterfall, which is especially beautiful when framed by fall’s hues. An easy trail leads directly to the falls.
Rock Hall
Rock Hall offers a completely different seasonal experience, where the show is as much about the water and wildlife as it is about the trees. The transformation here arrives late, with the trees and marsh grasses turning golden in early November. The air becomes crisp and salty, signaling the start of the great bird migration.
The must-see destination is Eastern Neck National Wildlife Refuge, a 2,200-acre island preserve. It's a vital stop on the Atlantic Flyway, and this time of the year brings a spectacular sight: the arrival of thousands of Tundra Swans, which gather on the water. You can walk the Tubby Cove Boardwalk to an observation tower for a wide-open view of the birds or hike the quiet Wildlife Trail through the marshes. Back in town, the community celebrates its heritage with FallFest in October. This lively outdoor festival fills Main Street with craft vendors, live music, and plentiful local oysters.
Middletown
The entire Middletown Valley is a perfect picture of autumn, a wide, flat basin framed on both sides by the long, parallel ridges of South Mountain and Catoctin Mountain. Around late October, these mountain walls ignite in a spectacular display. A drive along the Historic National Road offers a famous introduction as you crest Braddock Mountain and see the entire valley, dotted with farms, spread out below you.
This area is a haven for hikers. The Appalachian Trail runs along the crest of South Mountain, providing access to two iconic viewpoints. At Washington Monument State Park, you can climb the nation's first monument to George Washington for a stunning 360-degree vista. A few miles south on the trail is Gathland State Park, where the dramatic War Correspondents Arch frames a gorgeous view of the landscape. For a classic harvest experience, Jumbo's Pumpkin Patch (open from late September through October) is a local institution, offering hayrides to its sprawling fields to pick your own pumpkin.
Chesapeake City
Chesapeake City, a historic village split by the massive C&D Canal, sees its colors peak around the very end of October and into early November. The town's 19th-century architecture looks its best when framed by the changing leaves, and the wide canal acts like a mirror, reflecting the golden hues from its banks. A wonderful, easy way to see this is by walking the Ben Cardin C&D Canal Trail, a 1.8-mile paved path that runs right along the water's edge, offering perfect views of the boats passing by under the bright trees.
For one of the most dramatic views in the state, go on a 30-minute drive to Elk Neck State Park. The easy Turkey Point Lighthouse Trail takes you on a short walk out to a 100-foot bluff. From the lighthouse, you get a stunning, wide-open panorama of the Chesapeake Bay and the Elk River, surrounded by miles of colorful forest. For a classic harvest-time trip, Milburn Orchards in nearby Elkton hosts a Fall Festival with hayrides, apple picking, and a large corn maze.
Maryland's fall foliage season moves across the state. It starts in the western mountains around Oakland and Cumberland, then continues to the valleys and festivals near Thurmont and Middletown. The colors then move east, to the farm-focused areas of Mt. Airy and Hampstead, before finishing by the water in Havre de Grace, Rock Hall, and Chesapeake City. Each town offers a great way to get outdoors and see the changes. If you are looking for the best Maryland towns to explore in fall 2025, these cities are a must-visit.
