East Bayside Trail Fest

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:

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

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: