3 cycling events in New Gloucester, Maine
From big races to Saturday morning group runs—find cycling events and connect with the local endurance sports community.
New Gloucester
3 events in New Gloucester-
Sun, Jun 21, 2026 at 9:00 AMSee full details
We’re thrilled to announce the addition of a brand-new gravel ride presented by Pinebury to the 2026 Trek Across Maine! On Sunday, June 21, riders can take on either a 25-mile or 50-mile gravel route, starting and ending at Pineland Farms in New Gloucester.
GRAVEL ROUTE: Click here to access Ride with GPS files.
VOLUNTEERS NEEDED! - We are still looking for a few volunteers! If you are interested contact Emily at [email protected].
Trek Across Maine Gravel Timing:
The Trek Across Maine Gravel is a professionally timed event with a prompt/hard start time. While no prizes will be awarded, participants will earn something even better—bragging rights for their finish time and accomplishment on the course.
Gravel riders will also get the full Trek experience—they’ll cross the finish line alongside the participants completing the 3-day Trek Across Maine, making for a truly unforgettable celebration to close out the weekend.
Whether you’re new to gravel riding or a seasoned adventurer, this new option brings fresh excitement to our 42nd annual event.
Registration is $50 with a minimum of $100 fundraising.
Event-day registration: $65 with a minimum of $100 fundraising.
[Gravel Guide 2026 (2).png]
Interested in riding our three-day, 180-mile ride? Check out the details at TrekAcrossMaine.org.
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Sat, Aug 08, 2026 at 10:00 AMSee full details
Download Course files
Short Course: https://strava.app.link/lN12uUb4LLb
Long Course - https://strava.app.link/w5sfXrf4LLb
Event Website: www.mainelygravel.com
The Mainely Gravel ride is an event for all riders and is designed to challenge everybody on a mixed surface route over rolling hills. The gravel sections are everyday roads and can be ridden with either a road bike (30+mm tires ,recommended) or a gravel bike. PEDAL ASSIST BIKES are allowed but riders using such are not eligible for prizes. The dirt road surfaces can vary day to day depending on weather conditions and pot hole development. Please know that the last 5 kilometers of the route are on Pineland Farms xc ski trails that are well maintained and mown but could prove tricky on a road bike.
This year there are two course length options. The Long Course is 58 miles, and the short course (35 miles) is per the Long Course until mile 25 when the Short Course riders head for home while the Long Course riders do a 20-mile loop and then come back to hit the final 7 miles per the short course.
Registration check-in opens the day of the race at 8:30 with the mass start at 10:00. Riders will start en masse on Pineland Farms’ Oak Hill field adjacent to the parking lot. Please line up per your attitude toward the ride (Race? Ride? Adventure?). There is a lead car neutral start as the ride exits the 300 yards of the starting Oak Hill field and heads down Route 231 until the right hand turn onto Doughty Road.
Post race we are organize a gathering complete with food, drink and music. Food is provided by the Pineland Farms Deli and can be ordered on this registration page. Music is performed by local bands and we love giving them exposure. During the gathering we will have the awards presentation for Mainely Gravel short and long courses for all divisions. Our timing and results are handled by Eleven 11 Timing (www.eleven11timing.com) who do an absolutely wonderful job.
USA Cycling membership is not required for this ride.
Safety is paramount so follow the rules of the road. There will be road crossings. Stop! Check for traffic. The roads are open so stay right especially on blind sections such as corners and rolling hills.
Plenty to do at Pineland Farms. Bring the family who can enjoy a hike or run on the trails while registrants are out riding. Guests can buy lunch at the Pineland Farms market.
Port-a-johns are adjacent to the Oak Hill field parking lot.
Finally, Downeast Racing donates $5 of every registration to Independence Association (IA) which, for the last 60 years, has been dedicated to assisting adults and children with disabilities in obtaining full and inclusive lives in their chosen communities. As you will notice, we have included a donation option on the registration page. All donations (none too small!!) are used to enhance the programs for the Independence Association clients. Independence Association (IA) does fabulous work assisting those with disabilities lead full lives in the communities of the Maine Midcoast Region. Supervised independent living homes and apartments, outreach programs, work training, multiple physical fitness activities, friendship and caring. Mainely Gravel, through the generosity of its participants, has raised over $11,000 for Independence Association. We and the gang at IA thank you!!
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Sun, Jun 20, 2027 at 9:00 AMSee full details
We’re thrilled to announce we will be back in 2027 with our 2nd annual gravel ride presented by Pinebury! On Sunday, June 20, 2027, riders can take on either a 25-mile or 50-mile gravel route, starting and ending at Pineland Farms in New Gloucester. The gravel ride offers the perfect blend of challenge and adventure, whether you’re new to gravel cycling or a seasoned rider looking for something fresh. Gravel participants will still enjoy the full Trek experience—crossing the finish line alongside those completing the 3-day Trek Across Maine for an unforgettable celebration.
The updated route will be posted on TrekAcrossMaine.org once available.
Registration is $50 with a $100 fundraising minimum, or $65 on event day with the same fundraising requirement.
Volunteers are needed—please contact Emily at [email protected].
Interested in riding our three-day, 180-mile ride? Check out the details at TrekAcrossMaine.org.