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East Bayside Trail Fest

Sun June 22, 2025 Portland, ME 04101 US Directions

Events

Trail to Ale 10K

$50 9:15AM EDT - 11:30AM EDT Price increases after June 20, 2025 at 11:59pm EDT

Bayside Ride

$50 9:00AM EDT - 12:00PM EDT Price increases after June 20, 2025 at 11:59pm EDT

Trail Mix 2-Miler

$15 9:30AM EDT - 11:00AM EDT Registration ends June 22, 2025 at 11:59pm EDT

Place

38 Diamond Street
Portland, ME US 04101

Description

East Bayside Trail Fest, presented by Kennebec Savings Bank

On Sunday, June 22nd, support Portland Trails and the Bicycle Coalition of Maine at this first annual, one-of-a-kind event in the heart of the East Bayside neighborhood. A collaboration between nonprofit organizations and local businesses, the East Bayside Trail Fest, presented by Kennebec Savings Bank, consists of three events: the Trail to Ale 10K, the Bayside Ride, and the Trail Mix Two-Miler. The events will be staggered throughout the morning and will culminate in a community celebration on Diamond Street featuring music, food trucks, local beer, cider, and spirits, and more!

Is the registration fee a barrier to you? We're excited to partner with our friends at Northeast Runners Alliance for the Shared Miles Program to offer a limited amount of waived entries for our 10K and 2-Miler. If you or someone you know is interested in learning more, please reach out to Lindsay Conrad at lindsay@trails.org.

Interested in Volunteering? We need great people to join our crew! Volunteer Sign-Up

Trail to Ale 10K, presented by Martin's Point Health Care

That's right – the Trail to Ale 10K is back! This race was a favorite among locals back in the day, and now it's returning with an updated course, new start and finish lines, and a bigger post-race party. The scenic course features views of Casco Bay, Back Cove, and Portland's iconic skyline. Registration for the Trail to Ale 10K includes a beverage from a participating brewery or distillery at the East Bayside Trail Fest post-race celebration. This race is timed and will present awards for age groups at the finish line.

All participants in the Trail to Ale 10K receive 2 FREE DRINK tear-offs on their bibs to use at our brewery partners: Orange Bike Brewing, Rising Tide Brewery, Three of Strong Spirits, Hi-Fidelity Brewing

10K participants also get discounts at local favorites Toad&Co, Bite Into Maine, and food at Hi-Fidelity Brewing.

Event details:

Registration: $50

Packet pickup information:

  • WHERE: 38 Diamond St, Portland ME 04101 (Portland Trails Office)
  • WHEN: Saturday June 21 (9am-12pm), Sunday June 22 (7am-9am)

Course Info:

  • Start at 175 Anderson St (9:15am)
  • Finish at 34 Diamond St
Race course:

Bayside Ride, presented by Mann Law

Join us for a brand new event – the Bayside Ride! This a casual, non-competitive group bike ride with scenic views of Casco Bay. With 15-mile and 30-mile route options, the ride will head north through the towns of Portland, Falmouth, Cumberland, and Yarmouth. Rest stops will be positioned along the way with refreshments. Cyclists of all skill levels are welcome to participate! Registration for the Bayside Ride includes a beverage from a participating brewery or distillery at the East Bayside Trail Fest post-race celebration. Note: E-bikes are welcome! This ride is not timed.

All proceeds from the ride will support the Bicycle Coalition of Maine's work advocating for safer cycling, walking, and rolling throughout the state. 

Participants in the Bayside Ride receive 2 FREE DRINK tear-offs on their bibs to use at our brewery partners: Orange Bike Brewing, Rising Tide Brewery, Three of Strong Spirits, Hi-Fidelity Brewing

Bikers also get discounts at local favorites Toad&Co, Bite Into Maine, and food at Hi-Fidelity Brewing.

Event details:

Registration: $50

Packet Pick-Up Information:

  • WHERE: 38 Diamond St, Portland ME 04101 (Portland Trails & Bicycle Coalition of Maine Office)
  • WHEN: Saturday June 21 (9am-12pm), Sunday June 22 (7am-8:50am)

Course Info:

  • Start at 175 Anderson St. (9:00am)
  • Finish at 34 Diamond St.
15-mile course: https://ridewithgps.com/routes/51088764

 

30-mile course: https://ridewithgps.com/routes/51088766

Trail Mix 2-Miler, presented by Martin's Point Health Care

The Trail Mix Two Miler is a family-friendly fun run and walk on the trails. All ages and skill levels are welcome! This two-miler is perfect for...

  • Families – including strollers!
  • Anyone who is new to trails
  • People getting into (or returning to) running

This event isn't timed. Instead of being a competition, the Trail Mix will focus on fun and camaraderie. And then once you cross the finish line, it’s time to party!

All proceeds benefit Portland Trails and their work to create connections between neighbors, communities, and the natural world through their 100-mile trail network.

Breweries on Diamond Street will be opening early! Trail Mix 2-Miler are welcome to visit our brewery partners to purchase their favorite post-race drinks: Orange Bike Brewing, Rising Tide Brewery, Three of Strong Spirits

2-Mile participants also get discounts at local favorites Toad&Co, Bite Into Maine, and food at Hi-Fidelity Brewing.

Event details:

Registration: $15 – discounted rate available for families of four or more!

Packet pickup information:

  • WHERE: 38 Diamond St, Portland ME 04101 (Portland Trails Office)
  • WHEN: Saturday June 21 (9am-12pm), Sunday June 22 (7am-9am)

Course Info:

  • Start at 34 Diamond St.
  • Finish at 34 Diamond St.
Course Map:

Race Contact Info

If you have any questions about this race, click the button below.

Title Sponsor

Trail to Ale 10K Presenting Sponsor

Trail Mix 2-Miler Presenting Sponsor

Bayside Ride Presenting Sponsor

Trail to Ale 10K Gold Sponsors

Trail to Ale 10K Silver Sponsors

Trail Mix 2-Miler Silver Sponsor

Bayside Ride Silver Sponsors

Trail to Ale 10K Bronze Sponsors

Trail Mix 2-Miler Bronze Sponsors

Neighborhood Partners

Radio Partner

Thank you for supporting our organizations!

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