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4-day Peak Leaf Season Cumberland Bikepacking Loop!

$250.00

Mon Oct 19, 2026 8:00 AM - Thu Oct 22, 2026 4:00 PM

Come join us for a thrilling long weekend bikepacking adventure start/ending in Cumberland, Maryland! It'll be peak leaf changing season in Maryland which means this will be the best time for cycling through the canopy of green, yellow and orange colors. This event is perfect for outdoor enthusiasts looking to explore nature, be moderately physically active, have plenty of time to stare at the trees, and make new friends. We'll start our journey at the Visitor Center in Cumberland, Maryland, at the end of the C&O Canal towpath and head east to explore more of Maryland scenic roads and forestry. 

Whether you're a seasoned bikepacker or new to the sport, this event is suitable for all skill levels. Pack your camping gear, snacks, and a sense of adventure as we embark on this unforgettable trip together. Don't miss out on this opportunity to disconnect from the hustle and bustle of city life and immerse yourself in the great outdoors!

Mon Oct 19, 2026 8:00 AM - Thu Oct 22, 2026 4:00 PM

Come join us for a thrilling long weekend bikepacking adventure start/ending in Cumberland, Maryland! It'll be peak leaf changing season in Maryland which means this will be the best time for cycling through the canopy of green, yellow and orange colors. This event is perfect for outdoor enthusiasts looking to explore nature, be moderately physically active, have plenty of time to stare at the trees, and make new friends. We'll start our journey at the Visitor Center in Cumberland, Maryland, at the end of the C&O Canal towpath and head east to explore more of Maryland scenic roads and forestry. 

Whether you're a seasoned bikepacker or new to the sport, this event is suitable for all skill levels. Pack your camping gear, snacks, and a sense of adventure as we embark on this unforgettable trip together. Don't miss out on this opportunity to disconnect from the hustle and bustle of city life and immerse yourself in the great outdoors!

The Details

Date/Time:

Monday October 19th, 2026 8:00 AM → Thursday October 22nd, 2026 4:00 PM (stay up to date in the Signal group for time changes)

Days/Nights:

4 days/3 nights

Start/End Location:

Cumberland, MD, Visitor Center -> Cumberland, MD, Visitor Center/Washington D.C.

Total Mileage:

200+ miles

Cost to Participate:

Camping Admission: $250 (early bird) $265 (regular)

Type of Adventure:

Unsupported, group bikepacking along the canal to 3 hiker-biker campsites with non-potable water, portapotties, and picnic tables. There is no electricity at these sites so pack battery packs and a water filter. 

Terrain:

This will be a mix of local and gravel roads and ending with the GAP Trail which is paved. When it rains in Maryland it can get quite muddy, so bring fenders. A gravel bike is ideal for this path since we will be off-roading a good chunk of the time. It will be an adaptation of the Allegheny Crossroads Bikepacking Loop from BikepackingRoots.org

Difficulty:

Intermediate/Difficult. We will be biking for +/-6 hours each day. Decent fitness is required for this trip- this is not a race, but with lunch, rest and refill stops planned along the way, a 10mph pace with all these stops included will result in about 8 hours of moving day.

Gear Required:

A full gear list and detailed itinerary will be emailed to all participants before the start of the event. You should expect to carry everything that you think you will need on your bike for this trip. That includes, but is not limited to, a fully functioning bike, a tent, biking clothes and camping clothes, food and water, spare bike parts and tools, etc.. If you would like to see everything I brought to New Zealand for a 3 month tour (different from bikepacking, but packing lists are similar) you can watch a full breakdown here https://youtu.be/g60vVx2L2i8?si=nXkYML5pjf_DU2Yz.

FAQ

What will our lodging be for this trip? We will be staying at campsites along this trip. 

How Do I Know If My Bikepacking Rig Will Work? I will send out a Google Forms that must be completed to ensure that your bikepacking rig is well suited for this trip. I know some people will be new to bikepacking, so I want everyone to have a basic guideline of what is expected to be in your setup! You can find some informational videos on this playlist I made to help you prepare for the trip!

Can I Rent a Bike/Gear? Short answer- no. This trip is dependent on you packing/bringing your own bike and gear. I will send out a gear/equipment list before departure to all registrants. I do have a limited bike/gear supply closet, so if there is something you need, I might be able to offer a bit of help!

Who Is This Trip Targeted For? Anyone can join, but this route is specifically suitable for beginner/intermediate cyclists/bikepackers, or people who simply want a bit of a chiller bikepacking trip, one with more downtime to enjoy the surroundings, but still some hours of pedaling to get a sweat going.

What Happens If It Rains? Unless there is torrential downpour and a gigantic storm looming, this event is rain or shine, so pack accordingly!

How Do I Get To/From The Event? You can take the Amtrak and arrive to Cumberland the day before the event and rent a hotel (there is only one Amtrak a day going to/leaving from Cumberland). In Cumberland we will be reserving a shuttle with Wheelzup Adventures to drive us back to Washington D.C. together, so you do NOT need to book an Amtrak train back from Cumberland, MD.

What is your refund policy? If you cancel your trip 5+ weeks before our departure date, then you will get a full refund. If you are a no show or cancel less than two weeks before departure date, you will not get a refund (unless special circumstances occur).

What are the chances/conditions that this trip will be canceled? All trips require a minimum of 5 guests to sign up. If fewer than 5 guests sign up, then the trip will be canceled and I will refund all tickets. I recommend booking a refundable Amtrak ticket.

Do you have any other videos to help me know what this event may look like? Yes! Please check out past group trips here, and other videos such as biking across the United States, New Zealand, and other adventures.