2026 Crooked River Rambler (Maine Gravel Series)

The 3rd Annual Crooked River Rambler

Join us for a proper Western Maine gravel adventure at peak fall foliage! Explore the most beautiful gravel roads and quirky rural delights that the Crooked River watershed has in store…and have fun doin' it!

What's new for 2026

• Same route: The same great route (if it's not broke…)
• New extension: For those who want to keep on Ramblin', a new 10-mile "Crooked-Kezar Extension" is on offer, details below
• Community partnership: To pile on this year's Kezar love, we're adding a new community partner, the Greater Lovell Land Trust!
• New logo: A friggin' rad new Crooky logo and t-shirt courtesy of our friend and amazing local artist, Amy Borch
• Better snacks: And the snacks keep getting better!

The Highlights

• Scenic views: Pedal by half a dozen remote ponds in a lush Maine pine forest
• Mountain views: Soak in epic mountain views from your high gravel perch
• Historic roads: Conquer historic farm roads and ATV trails
• Mythical sights: Ponder the mythical “Hand on the Rock”
• Kezar Gorge: Gaze into the depths of the legendary Kezar Gorge

Event Overview

This ride is not a race. It's designed to bring people together around a shared love of the outdoors and provide an opportunity to challenge yourself, explore a new place, and hopefully make a few new friends! Read on for more specifics, but know this: the route is mostly sane, at times a lil' chunky, and may make you laugh (hopefully not cry, but no promises).

Rules

1. Be safe
2. Have fun
3. Get shit done
4. Don't take yourself too seriously

What's included in my registration fee

• Parking: Parking for the ride
• Camping: Free Camping
• Sticker: A sweet “Crooked River Rambler” sticker
• Meal: Post-ride meal (with options for all diets) provided by the wonderful Franck's Foods

Venue

This event will take place at Headwaters Basecamp, a new rural recreation hub in the foothills of the White Mountains and high in the Crooked River headwaters region. Everything before and after the ride will take place at this location. Here there will be a check-in tent, water, porto-potties, and food (coffee and baked goods before the ride, food truck after the ride). This is also where you will park for the event, and stick around for the afterparty!

The Ride

• Start time: 10am start, don't be late! (Check-in starts at 9am)
• Aid stations: 3 Aid-Stations with yummy snacks, water, and enthusiastic dancing fishes
• Route distance: The OG Crooky route is 33 miles, 65% off pavement, and a hell of a lot of fun. Checkout the full route here. There is also a strategic shortcut at the halfway mark for those who'd prefer a shorter (23 miles) ride.
• Extension: New this year: The “Crooked-Kezar Extension": An optional 10-mile addition that brings you further into the Kezar River watershed. Here's the route plus the extension.

Recommended Bike/Gear

• Preparedness: All riders should be prepared and self-sufficient! Bring spare tube, pump/c02, patch kit, tire irons, repair tool.
• Hydration: Bring plenty of water storage capacity and snacks. Distances between water refill and snack stations may be up to 15 miles.
• Bicycle type: It is recommended you ride this route with a bicycle. If you have a gravel bike, that'll definitely work.

After Party

Following the ride, there will be food, libations, yard games, and music back at Headwaters. Capping the night off with a campfire and s'mores for those who choose to spend the night! Music this year by the hyper local (down the road!!) musical wonder: Keith Briggs!

Camping

Free car, tent, van, bus camping to anyone who wants it Saturday and Sunday night. Saturday night you'll mostly be on your own, while Sunday night we'll be having a campfire with s'mores. Bring everything you need!

Safety

Unfortunately, riding a bicycle, particularly on roads also traveled by cars, can be a dangerous activity. We take safety at this event super seriously and we hope you will too. Our safety measures include:

• Emergency plan: An emergency plan to be shared with all riders prior to ride day.
• Med team: Our med team will be riding sweep.
• Check-in: Check-in and check-out to ensure everyone makes it off the course safely.
• First aid: First aid kit available at all aid stations and at basecamp.

Volunteers

Aren't much of a biker, but still want to be a part of the fun? Give us a hand by parking cars, handing out snacks, or retrieving directional arrows after the ride. Select “Volunteer” on the registration page and get a free meal ticket in return!

Community Partners

The Crooked River is the beating heart of the Sebago Lake watershed. Local partners like Mahoosuc Land Trust, Greater Lovell Land Trust, and Sebago Clean Waters are working hard to protect the Crooked River headwaters.

Financial Transparency

The Crooked River Rambler is put on by Headwaters Maine, LLC: a recreation basecamp business owned by husband and wife Jordan Rowell and Haley Cushing. We keep registration costs to the bare minimum and send $100-200 to each community partner after the event.

Event Details

Date: 2026-10-11
Location: 613 Sawin Hill Rd, Unorganized Territory of South Oxford, ME

Visit our registration page for more information!