10 Autumn-Ready Maryland Towns For A Weekend Retreat
Maryland’s scenic landscapes transform into a breathtaking tapestry of gold, amber, and scarlet as fall settles in, making it the perfect time to explore its charming small towns. From the rolling hills of the Piedmont to the quiet shores of the Chesapeake Bay, the state offers a variety of cozy destinations where crisp air, crunchy leaves, and seasonal flavors set the tone for an unforgettable weekend escape.
Autumn in Maryland means apple picking in historic orchards, sipping spiced cider at local farmers' markets, walking through corn mazes and pumpkin patches, and leaf-peeping vibrant forests ablaze with color. Whether you crave outdoor adventure in Cumberland or peaceful waterfront views in Oakland, these autumn-ready Maryland towns make for a perfect weekend retreat, showcasing the Old Line State's fall magic.
Havre De Grace
Havre de Grace is a beautiful town at the Susquehanna River-Chesapeake Bay confluence, which earns a new lease of life in autumn as the countryside gradually changes color and the community ushers in the season with fun festivals. Dazzling shades of mustard, amber, and crimson blanket Susquehanna State Park, luring leaf-peepers to experience the magical scenery along quiet trails covered in crunchy leaves. Furthermore, you can delight in the crisp air at Millard Tydings Memorial Park, which has peaceful walking paths overlooking the mouth of the Susquehanna River.
The Fall Harvest Festival is one of the best times to visit Havre de Grace. It helps spread the cheer in the community through pumpkin displays, craft exhibitions, food vendors, apple cider tastings, and live music in downtown. Lastly, you can spend the night at Vandiver Inn, a short walk from the Chesapeake Bay.
Cumberland
This Western Maryland town, tucked down in the foothills of the Allegheny Mountains, boasts an exquisite display of fall foliage that takes over its rolling landscapes. As the forested mountains in the backcountry transform into a sea of reds, yellows, and oranges, enthusiasts board the Western Maryland Scenic Railroad to witness the changing colors. The crisp air invites vacationers to embrace the open spaces, and Constitution Park offers a quiet space where you can sit under the shade and watch ducks swimming on the on-site pond.
The weekly Canal Place Farmer’s Market gets more vibrant in the fall as local farmers reap their agricultural bounty. For the icing on the cake, you can spend your night in Cumberland like a king by sleeping at the Hampton Inn Cumberland.
Hampstead
This Carroll County town welcomes autumn with stunning leaf colors and various family-friendly activities. Home to the Prettyboy Reservoir Park, leaf-peepers get front-row seats to the transitioning herbage during hiking, hunting, fishing, and boating excursions on the beautiful reservoir. Elsewhere, Deep Run Farms welcomes travelers for autumn-themed fun, featuring everything from pumpkin-picking to wagon rides, making for the perfect family-friendly activity.
The Hampstead Fall Festival is an excellent reason to visit the town in autumn, treating locals and foreigners to unmissable events and activities, including scarecrow making, food vending, hayrides, and a petting zoo. Finally, book your stay at Days Inn by Wyndham-Westminster for a restful night's sleep.
Mt. Airy
Mt. Airy provides a quiet escape from the busyness of Washington, DC, and Baltimore, allowing vacationers to slow their roll during a fun-packed weekend escape. The town houses several sprawling farms, which turn into popular fall playgrounds. At Gaver Farm, tourists can attend the Fall Fun Festival, which incorporates a variety of entertaining activities, such as corn mazes, pumpkin patches, and jumping pillows. Also, shopping at Knill's Farm Market allows first-timers to sample the town's impressive harvest and interact with the welcoming locals.
But for those interested in watching the leaves change color, you can head to Audrey Carroll Audubon Sanctuary to roam over a tranquil 129-acre sanctuary with woodlands, wetlands, and meadows. After a long day of exploring Mt. Airy, Budget Inn invites guests to spend a peaceful night without blowing the budget.
Oakland
Oakland's supreme natural scenery, punctuated by state parks, waterfalls, and a sprawling lake, culminates in one of the best autumn-ready Maryland towns for a weekend retreat. The town is famously home to Swallow Falls State Park, which easily harbors some of the best scenery in the state's countryside. It gets even better when the leaves start changing color, with the brilliant colors reflecting off the glassy waters of Muddy Creek Falls. The Oakland Golf Course offers a lovely escape for anyone seeking to enjoy autumn's crisp air, with rolling greens and manicured fairways letting you test your skills on 18 challenging holes.
Oakland also holds the Autumn Glory Festival, which celebrates the coming of the harvest season through parades, a farmers' market, craft exhibitions, and live music, among other fun activities. When you need a casual spot to spend the night, Oakland Motel easily fits the bill.
Thurmont
Thurmont is a secluded little town near the Pennsylvania border, known for its mountainous landscapes with dense woodlands. This rich green leads to glorious visuals when the autumn season comes around, and leaf-peepers come in their thousands to witness the transition at Catoctin Mountain Park. Covering over 5,000 acres, the reserve offers scenic drives, hiking trails, and fantastic overlooks of the beautiful fall foliage. The Catoctin Mountain Orchard is a popular fall destination for apple and pumpkin picking, with guests enjoying cider samples to help spread the season's cheer.
Thurmont also stages the annual Catoctin Colorfest, designed to celebrate the magic of fall foliage with pumpkin patches, corn mazes, craft vendors, and other family-friendly activities. When you have to call it a night, try staying at the grandiose Inn at Springfield Manor.
Rock Hall
Rock Hall lies along the shores of the Chesapeake Bay, welcoming vacationers to spend the fall weekend in a serene waterfront setting with boundless scenic views. The harvest season ensures you get more vistas than the water, especially when visiting the Eastern Neck National Wildlife Refuge. This 2,200-acre island explodes into a spectrum of brown, red, and yellow patches that dramatically reflect off the Chester River. Alternatively, you can watch the foliage from the water during an easygoing sail courtesy of Rock Hall Yacht Club.
The Rock Hall Fallfest is one of the major autumn celebrations in the town, with residents and foreigners coming together to mark the occasion with great food, crafts, live music, and kids' entertainment. For comfortable lodging, the waterfront Inn at Haven Harbour guarantees a remarkable experience.
McHenry
McHenry is a small town in Garrett County, known for housing the world-class Wisp Resort. This famous resort not only provides a supreme accommodation experience, but also fun activities for your fall getaway, including experiencing the fall colors at its Wisp Mountain Adventure Park. The establishment also hosts its annual Wisp Oktoberfest, where guests get to enjoy authentic Bavarian dishes, seasonal beer flavors, live music, and other harvest festivities.
Beyond the resort, McHenry provides more locations for leaf-peepers, including Sang Run State Park. This beautiful wilderness harbors miles of trails that wind through over 200 acres of changing tree leaves.
Middletown
Middletown is a historic community in Frederick County, but its natural spaces take precedence when autumn comes around. Many tourists prefer to venture into the great outdoors for front-row vistas of the changing leaves at Middletown Park. This serene escape offers walking trails, fishing spots, picnic areas, and ball fields. A tour of Mazzaroth Vineyard allows first-timers to enjoy delicious craft wines in a serene setting with rolling landscape views and fresh countryside air.
Meanwhile, Summers Farm welcomes travelers for its Fall Festival, marked by a lineup of entertaining encounters, such as pig races, hayrides, barnyard animals, and jumping pillows. Lately, don't hesitate to book Hollerstown Hill Bed and Breakfast in nearby Frederick for your nightly stays.
Frostburg
Frostburg is a charming college town in Western Maryland, and its atmosphere goes a notch higher in autumn with an influx of exciting festivities. Top among them is the Appalachian Festival, a long-held tradition of ushering in the leaf-peeping period with bluegrass music, film screenings, dance, and more. Besides the events, the town has tranquil natural spaces, including Frostburg Memorial Park, where tourists can find a nice spot to sit back, enjoy the outdoors, and watch people passing by.
However, one of the best ways to witness the fall foliage is to hop on the Frostburg Depot- Western Maryland Scenic Railroad for a mellow-paced ride on a vintage locomotive, exploring the sea of colors in the forested countryside. Lastly, Gunter Hotel, along Main Street, is a worthwhile accommodation in Frostburg.
As the leaves turn color and the air grows crisp, these autumn-ready Maryland towns for a weekend retreat come alive with autumn charm. From scenic hikes to harvest festivals and waterfront strolls, they all provide an excellent destination to savor the season in the United States. Whether you are chasing fall colors in Cumberland or simply seeking a peaceful weekend escape in Oakland, these lovely communities provide the perfect backdrop for cozy memories, long after you have left the state.
