Great Allegheny Passage (GAP) Trail Ramble

September 17-20, 2025 This fall, experience one of the most iconic trails in America: the 150-mile Great Allegheny Passage (GAP) trail. The 4 days of mostly car-free cycling along gently graded dirt and gravel trails will allow you to explore early-American history as we encounter viaducts and historic locations, along with local flora and fauna. Our journey begins in Cumberland, Maryland and ends in Pittsburgh, Pennsylvania where we will catch a shuttle back to our start point in Cumberland. Ramble Director: Bob Westgate Check out our Ramble's Early Bird and Group Discounts! A $300 deposit reserves your spot! Description Itinerary Planning Whether you are a new or veteran cyclist, this region and tour is ideal for you. Our fully supported tour will provide a one-of-a kind bicycle adventure and access to all the best parts of this area. What to Expect: This is a supported tour with camping, some indoor accommodations & optional indoor options, catered meals,  on-rou