All Outdoor Adventures
Likely to sell out
Cumberland, Maryland
Helmstetter’s Highball
Helmstetter’s Highball is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery front and center.…
Maryland guide
Maryland Outdoor Adventure Guide
Maryland has 57 tours across 5 cities, covering Cycling, Paddle Sports, Day adventure, and Hiking.
Explore this area
Explore All tours in Maryland, Cycling tours in Maryland, Hiking tours in Maryland.
Plan your adventure
Recommended itineraries
2–3 days
Weekend (2–3 days)
Base your weekend in Maryland and mix a highlight tour with one signature activity.
4–5 days
Classic (4–5 days)
Split time between Maryland and another nearby hub to sample multiple activities.
7 days
Deep dive (7 days)
Loop through three regions and layer in longer tours for a full-state perspective.
Top tours in Maryland
Likely to sell out
Cumberland, Maryland
Frostburg Flyer - 1309 Cab Ride
Frostburg Flyer - 1309 Cab Ride is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery front…
Likely to sell out
Train
Cumberland, Maryland
Ice Cream Train
Ice Cream Train is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery front and center. Expect…
Likely to sell out
Train
Cumberland, Maryland
Cottontail Comet
Cottontail Comet is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery front and center.…
Likely to sell out
Baltimore, Maryland
Louisiana Cajun Cooking
Louisiana Cajun Cooking is a guided outdoor experience based in Baltimore, Maryland that keeps the logistics simple and the scenery front and center.…
Likely to sell out
Cumberland, Maryland
Fireball Photo Experience
Fireball Photo Experience is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery front and…
Likely to sell out
Train
Cumberland, Maryland
CES Maryland Symphony Orchestra Train
CES Maryland Symphony Orchestra Train is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery…
Likely to sell out
Cumberland, Maryland
CES - Yarn
CES - Yarn is a guided outdoor experience based in Cumberland, Maryland that keeps the logistics simple and the scenery front and center. Expect a…
Best time to visit
Tour availability in Maryland varies by operator and activity, so check live calendars and choose dates that match your preferred pace.
What to pack
Plan for comfort and flexibility: bring layers, comfortable footwear, sun protection, and a refillable water bottle. Specific tours may recommend extra gear after booking.