Seasonal guide

Fall in Allegany County

Peak-colour drives, orchard stops, mountain overlooks and the best month of the year for the scenic railroad.

Spring Summer Fall Winter

What's on this fall

Live from the events calendar — nothing hand-typed, so it stays current.

Late September (single day)
Mountain Maryland 3M Challenge
The 3M Challenge is an annual multi-sport endurance event (biking, hiking/running, and paddling) organized by Mountain Maryland Trails along the Great Allegheny Passage and C&O Canal corridor near Cumberland. The 2026 event date has been set for September 26.
Select evenings and weekends, late November through December
The Polar Express™ Train Ride
Western Maryland Scenic Railroad recreates the classic story with a themed evening excursion from the historic Cumberland depot, featuring hot chocolate, storytelling, and a visit from Santa. Trains depart from the Western Maryland Railway Station in downtown Cumberland.
A weekend in September
Heritage Days Festival
Cumberland's Heritage Days Festival brings food trucks, arts and crafts vendors, live music, and historic re-enactments to downtown to mark the start of the fall season, per Cumberland Main Street.
Seasonally, spring through fall, with peak summer schedule (check WMSR calendar)
WMSR Frostburg Flyer
The Western Maryland Scenic Railroad's summer excursion, the Frostburg Flyer, runs steam- or diesel-powered vintage trains between Cumberland and Frostburg through the Cumberland Narrows and over the Helmstetter's Curve, offering scenic mountain views.
June-October, Thursdays 9:30am-2pm and Saturdays 9:30am-12:30pm
Downtown Cumberland Farmers Market
This seasonal open-air market on the Downtown Pedestrian Mall offers local produce, plants, baked goods, and locally raised meats from area growers. It runs Thursdays and Saturdays from June through October.
Annually on Memorial Day (last Monday in May)
Cumberland Memorial Day Parade & Observance
Cumberland-area veterans organizations and the City of Cumberland hold a Memorial Day parade and wreath-laying ceremony to honor fallen service members, typically processing through downtown to a local memorial or cemetery.
Annually on Labor Day weekend (early September)
Labor Day Community Events
Allegany County towns, including Westernport and LaVale, host community Labor Day events such as picnics, ballgames, and fire company gatherings marking the unofficial end of summer.
Weekends in October
Pumpkin Patch Limited
Western Maryland Scenic Railroad's fall excursion takes riders on a themed train trip tied to the pumpkin-patch/harvest season, departing from the Cumberland depot through the mountain scenery.
Evening event in late November
Downtown Cumberland Tree Lighting
Downtown Cumberland kicks off the holiday season with a tree-lighting ceremony on Baltimore Street, part of the city's annual holiday festivities promoted by Cumberland Main Street and Allegany County tourism.
Evening event in late November
Downtown Frostburg Tree-Lighting Ceremony
Frostburg's Main Street district holds an annual tree-lighting ceremony to open the holiday season downtown, as noted in Allegany County's official holiday events guide.
October 31, afternoon (1:00–4:00 PM)
Boo on the Bricks
A downtown Halloween event on Cumberland's brick-paved Baltimore Street pedestrian mall featuring trick-or-treating among Main Street businesses, listed on the Cumberland Main Street events calendar.

Best places in fall

Picked for the weather and the daylight.

History & MuseumsHistorical Landmark

"Great Allegheny Passage Mile 0 Cumberland, Maryland" Marker

Historical Landmark in Cumberland.

Historical Landmark

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History & MuseumsHistorical Landmark

"Our Local Indian Heritage" Marker

Historical Landmark in MD 21502.

Historical Landmark

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History & MuseumsTourist Attraction

"Welcome to Cumberland Historic City Center" Sign

Tourist Attraction in Cumberland.

Tourist Attraction

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Shopping & ArtisansSupermarket

ALDI

Retail chain selling a range of grocery items, meat & dairy.

Supermarket

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History & MuseumsNon-Profit Organization

Allegany Arts Council

Non-Profit Organization in Cumberland.

Non-Profit Organization

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ArchitectureCourthouse

Allegany County Courthouse

The county's courthouse building dates to 1894 on a site used for county courts since 1799, standing on Washington Street in the heart of the historic district.

Government building · Public building hours

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