Virginia Backcountry Ride
In partnership with Virginia Backcountry Cabins — the whole 135-acre property, just for our crew.
Oct 1–4, 2026 · Monterey, VA · Cabins & tent camping · All skill levels
The Ride
Four days based out of a private 135-acre backcountry property in Virginia's Allegheny Highlands. We've teamed up with Virginia Backcountry Cabins to take over their entire property outside Monterey, VA — no other guests, just our crew. The property backs directly onto thousands of acres of George Washington & Jefferson National Forest, putting real backcountry right outside the door. Days on the trail through Highland County — some of the least-populated, most remote backcountry in Virginia — nights around the fire pit back at camp.
Routes are being scouted now with Virginia Backcountry Cabins. Full daily routes and GPX files will be shared with confirmed riders as soon as they're finalized.
Where you'll stay — the whole property, just for us. Virginia Backcountry Cabins is ten individually themed cabins on a mile-long creek with fern glades and a shaded hollow. For this event we have exclusive use of the whole property.
Three lodging options: • Single Occupancy Cabin — $670 · your own themed cabin, private. 4 spots. • Double Occupancy Cabin — $415 per person · share a themed cabin with a riding buddy or partner. 10 spots (5 cabins × 2 people). • Tent Camping — $260 · pitch your own tent on the property. 10 spots.
All three include lodging or campsite for the nights of Oct 1–3, continental breakfast and dinner daily, and a daily trail snack pack (trail mix, protein bars, Gatorade). Lunch is on your own. Departure is Sunday, Oct 4.
Lodging and property provided by our partners at Virginia Backcountry Cabins, 840 Lower Back Creek Rd, Monterey, VA (virginiabackcountry.com).
What riders said
About our last weekend.
"Great event, well directed and organized by John and Anthony."
"Count me in for the next one!"
"Excellent routes, delicious food, and overall very professional. They really care about everyone in the group!"
AMA Sanctioned · Membership Required
Two Jackasses Moto Adventures is an official charter of the American Motorcyclist Association, and this event is AMA-sanctioned and insured. An active AMA membership is required to attend and ride — annual membership runs ~$49 if you don't already have one. Sign up here: Join the AMA. You'll be asked for your AMA member number at signup so we have it on file in case of an incident requiring an insurance claim.
Arrival & day-of
- Property: Virginia Backcountry Cabins, 840 Lower Back Creek Rd, Monterey, VA 24465. The whole 135-acre property is reserved for our group — no other guests.
- Arrival: Thursday, October 1. Roll in, pick up your cabin key or set up your tent, and meet the crew around the fire.
- Day-of contact: We'll send a final logistics note the week of the ride with the weather call and last-minute details.
Trip Outline
- Thu Oct 1 — Arrival day. Settle into your cabin or campsite, meet the crew. Campfire welcome dinner.
- Fri Oct 2 — Ride day 1. Backcountry route through George Washington National Forest.
- Sat Oct 3 — Ride day 2. Second route, different terrain. Group cookout back at camp that night.
- Sun Oct 4 — Continental breakfast and departure.
Included
- · Lodging or campsite for the nights of Oct 1–3 (choose your tier)
- · Continental breakfast and dinner daily
- · Daily trail snack pack (trail mix, protein bars, Gatorade)
- · Exclusive use of the Virginia Backcountry Cabins property for our group
- · Ride leaders on the road and route coordination
- · Community campfire nights back at camp
Good to know
- · Lodging & property provided by our partners at Virginia Backcountry Cabins (840 Lower Back Creek Rd, Monterey, VA · virginiabackcountry.com) — we have the whole place reserved for our crew.
- · Capacity is capped at 24 riders total: 4 single-occupancy cabins, 10 double-occupancy cabin spots, and 10 tent camping spots. Registration is first-come, first-served — once a tier sells out, it will not be reopened.
- · Lunch is on your own — we stop along the route, you order your own.
- · Open to all skill levels — most Highland County forest roads are beginner-friendly with room to push harder.
What to bring
- · Riding gear — helmet, jacket, gloves, boots
- · Basic tools + tire repair kit
- · Personal overnight bag (cabin riders) or tent + sleeping gear (camping riders)
- · Cash/card for lunches and fuel along the way
- · Rain gear and layers — early October in the highlands can swing cold
Your bike & skill
- · Open to all skill levels
- · Comfortable on gravel and forest service roads
- · Street-legal dual-sport or ADV bike, knobby or 50/50 tires
- · Solid mechanical condition — fresh tires, chain, brakes
Weather & cancellation
Rain or shine. Adventure riding happens in the rain — bring proper rain gear and dress in layers. The only weather cancellation is a severe storm that makes riding or driving genuinely unsafe. In that rare case, we'll reschedule or refund. Otherwise, the standard policy applies: full refund up to 30 days before the event.
Location
Virginia Backcountry Cabins, 840 Lower Back Creek Rd, Monterey, VA 24465Tap the address or map to open directions in Google Maps.
Common questions
Do I have to stay in a cabin, or can I tent camp?+
Either. This event includes single-occupancy cabins, double-occupancy cabins, and tent camping on the property. Pick whatever fits your budget and style.
How much does it cost?+
Pricing depends on lodging: $670 for a single-occupancy cabin, $415 per person for a double-occupancy cabin, or $260 for tent camping — all three include lodging/campsite for the nights of Oct 1–3, breakfast and dinner daily, and a daily trail snack pack, for the full Oct 1–4 event. Lunch is on your own. Registration is first-come, first-served with a hard cap of 24 riders — once a tier sells out, it will not be reopened.
What are the routes?+
Routes are being actively scouted with Virginia Backcountry Cabins right now. We'll share the daily routes with confirmed riders as soon as they're locked in.
What if it rains?+
We ride. Bring proper rain gear and layers — we only cancel for severe storms that make riding or driving genuinely unsafe.
How big is the group?+
Capped at 24 riders total: 4 single-occupancy cabins, 10 double-occupancy cabin spots, and 10 tent camping spots. Registration is first-come, first-served, and we will not add additional spots once each tier sells out.
What's your cancellation policy?+
If your plans change after your reservation is confirmed, cancellation notice is required 14 days in advance of your arrival date. If you cancel your reservation 14 days or less prior to arrival date, you are responsible for the entire cost of your reservation.
Question not answered? Drop us a line.
Reserve your spot
Virginia Backcountry Ride
October 1–4, 2026 · $260 per rider · starting
Cancellation policy
If your plans change after your reservation is confirmed, cancellation notice is required 14 days in advance of your arrival date. If you cancel your reservation 14 days or less prior to arrival date, you are responsible for the entire cost of your reservation. Your credit card on file will be charged in full.