If you’ve been following us, you’ve seen our post about the Cape Cod Challenge. We completed it last weekend… well mostly. More on that below.

The route’s history:

The 133 mile mountain bike route was created by Dave Lafreniere with support from Cape Cod NEMBA. The route was designed for a year-long competition in 2025 connecting trails from Woods Hole to Provincetown. It’s divided into four legs, each with two timed Strava segments. As Dave told us, “navigation and self-sufficiency are just as important as strong legs and big lungs”. Even though the official challenge has ended, the route remains. Portions of it get regular trail maintenance from the locals but many trails are less often ridden. For that reason, the route is an ambitious way to experience the trails covering the entirety of Cape Cod.

Our plan:

We’d been eyeing this ride for a year and finally found a three day window and more important, a ride from Provincetown back to Woods Hole. This wasn’t about leaderboards or KOMs. Our goals were simple: ride across the entire iconic stretch of Cape Cod, enjoy the adventure, and use it as training for a bigger trip ahead in July. With campgrounds not yet open, we opted for credit card camping and planned the trip as follows:

Day 1: Leg 1 // 36.4 miles

Day 2: Legs 2 & 3 // 64.1 miles

Day 3: Leg 4 // 42 miles

Our bike choice:

We toyed with the idea of drop bar bikes, but considering the route’s design and knowing there’d be winter storm damage, we decided mountain bikes made the most sense. One full suspension with 2.3“ tires and and one hardtail with 2.6”. This proved to be the right choice. While the route has sections where gravel bikes could work, there are too many long stretches of rocky trails and some sections of sand that would challenge the widest gravel tire bikes.

Our kit:

We packed fairly light as we knew there’d be tech trails that would be less fun on heavily loaded bikes. A second pair of bibs, cloths to sleep in, rain gear, tools, flat kit, medical kit, and toiletries. For reference, my gear plus the bags added 6.5 lbs before food and water.

Leg 1 is known for being the most rugged of the four, with infrequently traveled trails that feel equal parts forgotten path and hidden gem. The mix of technical terrain and early season conditions added to that character, especially in the first 17 miles which were the best trails of this leg.

After a quick roll off route for lunch, we hit sections that treated us with some hike‑a‑bike thanks to historic blizzards this past winter. Nothing unexpected, and nothing that we allowed to completely dampened the mood. Admittedly there were a few times the dense cape brush and razor sharp thorns pushed us to the brink, but we kept rolling.

Dense pine forest with a singletrack descent

We continued north, skirting along Rt. 28 until we reached Upper Cape Tech. We were told the trail would be blocked here. A recent fence and some construction added a bit more bushwhacking before we eventually found our way to the canal. The relief of a paved bike path was quickly met by a “gift” of cold drizzle and a steady headwind for the final 4 miles to our hotel.

The first leg was challenging, but never felt overwhelming. There was just enough fun singletrack to balance out all the hidden turns, sharp thorns and twiggy underbrush that slowed things down. Some sections of type‑2 fun and a fair amount of climbing, strangely about 1,000 ft more than what Ride With GPS claimed.

Day 2 began just before 8:00 a.m. and we tackled the first 20 miles in relatively dry conditions. The trails were amazing. We were treated to some of the best mountain bike trails the Cape has to offer in Maple Swamp. We veered off route again for lunch in West Barnstable only to get back on the bikes in a steady rain. We were well prepared with rain gear and pushed onward for the daunting task of another 45 miles ahead.

The next 15 miles were more great trails, but super slow due to weather and some confusing turns in close proximity to other trails. At one point, recent moto activity created a web of trails on an off camber section. It bordered on dangerous glancing at GPS while riding some of the route’s most technical terrain. Add in the sound of cars racing by on Rt 6 less than 20 yards away and you have a recipe for frustration. We finished leg 2 in relentless rain well behind our plan.

Knowing the rain would slow us down, we planned a bail out route in advance. With an expected finish in the dark and the temperature continuing to drop, the decision was easy to head toward the rail trail. This cut 9 miles off the route but saved over 2 hours of riding trails in the cold. While disappointed we didn’t get all of leg 3, we knew the decision was the right one. Sometimes a bit less miles and less dirt is better than an Uber ride, or worse.

Day 3 started at 8:30 a.m. with a quick ride over to Chocolate Sparrow in Orleans for breakfast, followed by a mellow bike‑path roll up to Coast Guard Beach. After a few photos of classic Cape Cod landmarks, we continued north through twisty cliffside trails that wind up to Marconi Beach, then inland toward Wellfleet.

The trails on the eatsern side of Wellfleet wind around some of the cleanest ponds and lakes on the Cape. Riding shifts between sandy doubletrack and tight, flowy singletrack. Truly some of the most fun trails on the entire route.

The final push includes a few more ocean viewpoints, a handful of punchy climbs, and sweeping downhills that pass by campgrounds and quiet pockets of forest you wouldn’t expect this far north. The approach into Provincetown mixes a stretch of tarmac before linking to an old abandoned rail bed that delivers you straight back to Commercial Street for a finish in front of Town Hall.

Our take on the route and why it might or might not be the route for you.

This is a great mountain bike route and not ideal for most gravel bikes. There are plenty of sections ridable with drop bars, but far more sustained lengths of rocky or sandy trails that favor mountain bike widths and suspension.

While it’s been done in by some riders in 2 or 3 days and a select few in 1 day, it’s best ridden over 4 days. It’s great as a four day bikepacking adventure but could be equally fun as 4 single rides without gear. If you decide to bikepack in season (May-Sept) book camping or hotels well in advance!

Leg 1 is all about type 2 fun and punchy climbs.

Legs 2 and 3 have some of the best mountain biking the Cape has to offer.

Leg 4 is picturesque riding and quintessential Cape Cod.

Do you need help planning this trip or another your considering?

We offer anything you could possibly need from advice on on gear and packing, guidance on nutrition and safety, support with rental gear, or help figuring out the logistics. If you need help, shoot an email to jr@adventurerideworks.com

To see more posts like this subscribe here and Follow us on social

You can find the original Cape Cod Challenge route details here

Huge thanks to Dave and CCNEMBA for creating something truly special. If you’d like to support their work, please consider donating to CCNEMBA here

Ride Report: Cape Cod Challenge

FOLLOW OUR ADVENTURES