East Bayside Trail Fest

Events

$50

$40

9:15AM EDT 11:30AM EDT

Registration Opens February 1, 2026 at 9:00am EST

$50

$40

9:00AM EDT 12:00PM EDT

Registration Opens February 1, 2026 at 9:00am EST

$15

9:30AM EDT 11:00AM EDT

Registration Opens February 1, 2026 at 9:00am EST

Place

38 Diamond Street
Portland, ME US 04101

Description

Kennebec Savings Bank East Bayside Trail Fest

On Sunday, June 28th support Portland Trails and the Bicycle Coalition of Maine at the second 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, and spirits, and more!

Interested in Volunteering? We need great people to join our crew! Email us at Fest@trails.org

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 at the after-party!

Event details:

Registration: $50

Packet pickup information:

WHERE: 38 Diamond St, Portland ME 04101 (Portland Trails Office)
WHEN: Saturday June 27 (9am-12pm), Sunday June 28 (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 the after-party!

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 27 (9am-12pm), Sunday June 28 (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.

Event details:

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