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-route SAG, luggage transportation, and evening activities. The weather should be nice and the scenery spectacular. We will traverse the Great Allegheny Passage Trail on this 155-mile, mostly car-free adventure. Daily mileage between 25-62 miles of low elevation gains gravel and dirt cycling. 
  

  Highlights

  • Nearly 100% off-road, 155 miles of riding on gravel and paved trails
  • Great Allegheny Passage Trail (155 miles)
  • Frank Lloyd Wright's Fallingwater
  • Options for all indoor accommodations

  What’s Included:

  • Welcome reception and orientation
  • 3 nights - 1 nights in hotel, 2 camping nights
  • 3 breakfasts, 3 lunches, 3 dinners
  • Snacks and beverages between meals
  • Full van and baggage transport
  • Experienced BIKEternity guides knowledgeable of the area
  • Daily route directions via GPX files for your GPS or phone app
  • Daily mileage options.

  Not Included:

  • Insurance of any kind
  • Guide gratuities
  • Alcoholic beverages
  • Bike rentals (BIKEternity will facilitate)
  • Personal bicycle shipments (BIKEternity will facilitate)
  • Transportation from/to local airport or train station

  Airport Information

  End: Pittsburgh International Airport (PIT)

  Amtrak Information

  Start/End: Cumberland, MD

  End: Pittsburgh Union Station, Pittsburgh, PA

  Parking Information

  Parking is available at the start point hotel for an additional fee.
  
  

• Day 1: Arrival/Orientation in Arlington, VA

  Arrive on your own in Cumberland, MD at our start point hotel by 4pm for the start of your Great Allegheny Passage (GAP) trail adventure; 4-days of blissful riding with awesome scenery. Early arrivals can checkout what the "Queen City" has to offer. We’ll have an orientation meeting at our hotel, enjoy dinner, and call it a night before the riding starts in the morning.

  Day 2: Cumberland, MD to Confluence, PA

  Miles: 32-62 miles · Elevation: +2,895’ / -2,191’

  Terrain: Gravel Trail

  Yesterday, we completed the C&O Canal Towpath. Today we begin the 150 mile Great Allegheny Passage trail with a gentle incline toward the Eastern Continental Divide. Along the way up the less than 2% grade we may see the steam or diesel engine from the Western Maryland Scenic Railroad alongside the trail. We’ll ride through the Borden, Brush and Big Savage (3300’) tunnels passing the Mason-Dixon Line between Maryland and Pennsylvania. Once we cross the divide, it will be easy riding toward Pittsburgh; but first we overnight along the river in Confluence, PA

  Day 3: Confluence to West Newton

  Miles: 27-53 miles · Elevation: +864’ / -1,416’

  Terrain: Gravel Trail

  We’ll continue our slight downhill journey along the Youghiogheny River as we pass through Ohiopyle State Park with its gorgeous high bridges and waterfalls. Some may want to take a tour of Frank Lloyd Wright’s Fallingwater architectural masterpiece (we offer a shuttle) or enjoy an ice cream at a local venue. We’ll see some of the most spectacular scenery of the trip today. Our accommodations are just a stone's throw from West Newton; a place where eateries and live music abound.

  Day 4: West Newton to Pittsburgh

  Miles: 20-36 miles · Elevation: +812’ / -858’

  Terrain: Gravel Trail, Paved Road

  Van transfer: 2 hour bus back to Cumberland for those needing to return to Cumberland

  Today is the last day of our adventure. We’ll complete the GAP Trail at “The Point”, Point State Park in Pittsburgh.The park sits at the confluence of the Allegheny, Monongahela, and Ohio Rivers. During the day we will ride toward McKeesport where the Youghiogheny and Monongahela Rivers converge and into more and more urban riding. After completing the trail, those returning to Cumberland will board a bus for the journey home; others will depart from Pittsburgh

• Ramble Tour Director: Bob Westgate

  Bike Shipping:

  Early Arrivals: For those arriving early the day(s) before the tour, we would recommend the following:
  

  
  

  Gear List: to be provided