Events in Freeport, Maine | 2026-2027

Boots and Brews 5K [runsignup.com]
Sat, May 16, 2026 at 9:15 AM
Description
Boots and Brews 5K & Kids’ Fun Run

A Celebration of Freeport’s Rich History and Vibrant Future

Join us for the annual Boots and Brews 5K and Kids’ Fun Run—a fun, family-friendly event celebrating...
Boots and Brews 5K & Kids’ Fun Run

A Celebration of Freeport’s Rich History and Vibrant Future

Join us for the annual Boots and Brews 5K and Kids’ Fun Run—a fun, family-friendly event celebrating Freeport's rich history and vibrant future! Once home to over 30 shoe and boot factories, including the iconic L.L. Bean, Freeport’s legacy as a hub of craftsmanship remains at the heart of the community. Today, the town thrives as a destination for craft beer lovers, outdoor enthusiasts, and history buffs.

The Boots and Brews 5K starts and ends in downtown Freeport, showcasing the beauty and charm of this historic town. After the race, stick around to sample brews from local favorites like Brickyard Hollow, Goodfire Brewing, Maine Beer Company, and Mast Landing Brewing. Plus, winners will take home a piece of Freeport!

That's not all all participants will be entered into a bib-draw to win a variety of Freeport Prizes as well as receive access to exclusive discounts from local businesses through our digital swag bag—a great way to enjoy even more savings in Freeport!

Race Day Schedule:
- Fun Run (Ages 12 & Under): 9:15 AM – 9:45 AM
- 5K Race: 10:00 AM – 12:30 PM
ONLINE REGISTRATION CLOSES at 11:59 PM on Wednesday, May 14th

Did you miss online registration? No problem! You can still sign up in person during packet pickup:
- Friday, May 16th from 4:00 – 7:00 PM at the L.L. Bean Flagship Store
- On race day at 23 Depot Street in Freeport
3.1 Miles 5k Fun Run Run
23 Depot St., Freeport, Maine, 04032, United States
OpenStreetMap Google Maps

L.L.Bean 4th of July 10K and 1-Mile Family Fun Run/Walk [runsignup.com]
Sat, Jul 04, 2026 at 7:25 AM

Description

Celebrate Independence Day by participating in the 49th annual L.L.Bean 4th of July 10K and 1-Mile Family Fun Run/Walk supporting the YMCA of Southern Maine Casco Bay Branch. Together, L.L.Bean and the YMCA are committed to building healthy, confident and secure communities for everyone to enjoy.

1 Miles 10k Fun Run Run Walk
Freeport, Maine, 04032, United States
OpenStreetMap Google Maps
Farm to Farm Ultra [runsignup.com]
Mon, Sep 14, 2026 at 12:00 AM

Description

The Farm To Farm Ultra Run is held on a looped course in Freeport, Maine on the Wolfe's Neck Center & Freeport Conservation Trust trails, but also includes four virtual options: 5 miles, 10 miles, 30...

The Farm To Farm Ultra Run is held on a looped course in Freeport, Maine on the Wolfe's Neck Center & Freeport Conservation Trust trails, but also includes four virtual options: 5 miles, 10 miles, 30 miles, and 50 miles. This event is part of the Maine Track Club Grand Prix Series, and participants are allowed to earn points for one virtual event in addition to or instead of the in-person race. If you intend to do both in-person and virtual, you must register separately for each event.

Click here to register for the in-person race on Sunday, Sep. 27 2026

The entry fee for each virtual event is $25, with no t-shirt included.

If you would like a shirt, please contact us! They are 15$ for local pickup (greater Portland area) or 20$ to ship.

Participant will have from Sep. 14 2026 to Oct. 12 2026 (Indigenous Peoples' Day) to complete their chosen distance(s) and submit results.

5 Miles 10 Miles 30 Miles 50 Miles Run Trail Ultra Virtual
184 Burnett Rd, Freeport, Maine, 04032, United States
OpenStreetMap Google Maps
Farm to Farm Ultra [docs.google.com] [Register at ultrasignup.com] - Facebook
Sun, Sep 27, 2026

Relay Ultra
184 Burnett Road, Freeport, Maine, 04032, United States
OpenStreetMap Google Maps

4 running, fun run, and ultra events in Freeport, Maine

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