2026 Crooked River Rambler (Maine Gravel Series)
Unorganized Territory Of South Oxford, Maine
- Date
- Sunday, October 11, 2026 at 10:00 AM
- Location
- 613 Sawin Hill Rd
Unorganized Territory Of South Oxford, Maine
04217
United States
OpenStreetMap Google Maps
About this event
The 3rd Annual Crooked River Rambler is here! 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
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The same great route (if it's not broke…)
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For those who want to keep on Ramblin', a new 10-mile "Crooked-Kezar Extension" is on offer, details below
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To pile on this year's Kezar love, we're adding a new community partner, the Greater Lovell Land Trust!
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A friggin' rad new Crooky logo and t-shirt courtesy of our friend and amazing local artist, Amy Borch
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And the snacks keep getting better!
The Highlights
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Pedal by half a dozen remote ponds in a lush Maine pine forest
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Soak in epic mountain views from your high gravel perch
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Conquer historic farm roads and ATV trails
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Ponder the mythical “Hand on the Rock”
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Gaze into the depths of the legendary Kezar Gorge
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
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Be safe
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Have fun
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Get shit done
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Don't take yourself too seriously
What's included in my registration fee:
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Parking for the ride
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Free Camping
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A sweet “Crooked River Rambler” sticker
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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 (more below)!
The Ride
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10am start, don't be late! (Check-in starts at 9am)
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3 Aid-Stations with yummy snacks, water, and enthusiastic dancing fishes
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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 strategic shortcut at the halfway mark for those who'd prefer a shorter (23 miles) ride. This is the bizzness!
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If you're one of those crazies who wants more…
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New this year: The “Crooked-Kezar Extension": An optional 10-mile addition that brings you further into the Kezar River watershed then loops you on back to the OG Crooky Route to finish off your ride back to Headwaters. This extension is for those piddle-pedalers who want to keep on pushin', blasting you on up to the finest hill country general store there ever was: the Center Lovell Market. Enjoy the Baldface views and a sneaky cute antique shop, then send it back down to the Kezar River valley floor and bring ‘er on home. Here's the route plus the extension.
Recommended Bike/Gear
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All riders should be prepared and self-sufficient! Bring spare tube, pump/c02, patch kit, tire irons, repair tool.
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Bring plenty of water storage capacity and snacks. Distances between water re-fill and snack stations may be up to 15 miles.
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It is recommended you ride this route with a bicycle. Although perhaps a unicycle or a tricycle could also work. As to what kind, that's up to you. If all you've got is a full-suspension mountain bike, that'll do. If you're one of those gear heads who has 8 bikes, surely one will also do. This route has been done on every kind of bike there is, including tandem bikes, commuter bikes, and old steel fixies. If you have a gravel bike, that'll definitely work. Run whatcha brung, ain't no shame heyuh.
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 as we will be setting up for the event. Sunday night we'll be having a campfire with smore's. There will be porto-potties and a water jug, otherwise 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 measure include:
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An emergency plan to be shared with all riders prior to ride day so they know what to do in the event of an emergency on the course
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Our med team will be riding sweep
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Check-in and check-out to ensure everyone makes it off the course safely
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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
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Why This Place Matters
The Crooked River is more than just a beautiful backdrop — it’s the beating heart of the Sebago Lake watershed. Its cold, clean waters are critical spawning grounds for landlocked Sebago salmon (Salmo salar sebago), a unique strain of salmon found only in the Sebago watershed. The river also helps supply drinking water to nearly 1 in 6 Mainers, making its health vital to communities far beyond its banks.
That’s why local partners like Mahoosuc Land Trust, Greater Lovell Land Trust, and Sebago Clean Waters are working hard to protect the Crooked River headwaters — keeping forests intact, water clean, and this incredible place thriving for generations to come.
In 2024, local paddlers and storytellers Andy Gagne and Jenny O'Connell and friends called attention to the river’s importance by paddling from its headwaters all the way to Casco Bay. Checkout their award-winning documentary, Follow the Water, made in partnership with Maine Mountain Media.
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. The goal for the event is first and foremost to have a great time with friends and explore this beautiful area we call home! We keep registration costs to the bare minimum, covering food, music, aid station supplies, stickers, and other random incidentals. We send $100-200 to each community partner after the event. Sometimes we're able to keep a couple hundred bucks to pay us for our time organizing, but that's really just a bonus.