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:
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:
May 16, 2026
Distance — Fun Run Boots and Brews (no BBQ)
Type — Running
09:15
$5.00
May 16, 2026
Distance — 3.1 Miles
Type — Running
10:00
$40.00
May 16, 2026
Distance — Non-Runner BBQ (under 21)
Type — Running
11:00
$5.00
May 16, 2026
Distance — Non-Runner BBQ 21+
Type — Running
11:00
$15.00
May 16, 2026
Distance — 3.1 Miles
Type — Running
-129 days remaining
$40.00
May 16, 2026
Distance — 3.1 Miles
Type — Running
-129 days remaining
$40.00
May 16, 2026
Distance — 3.1 Miles
Type — Running
-129 days remaining
$40.00
May 16, 2026
Distance — 0.5 Miles
Type — Running
-129 days remaining
$8.00
May 16, 2026
Distance — Fun Run Boots and Brews (no BBQ)
Type — Running
-129 days remaining
$5.00
May 16, 2026
Distance — Non-Runner BBQ (under 21)
Type — Running
-129 days remaining
$5.00
May 16, 2026
Distance — Non-Runner BBQ 21+
Type — Running
-129 days remaining
$15.00
These values represent the 3-year monthly averages for May in Freeport.
Learn more about the host city, Freeport.
Freeport is just north of Portland in Maine and hosts the headquarters of L.L Bean. Because of the popularity of L.L. Bean, other stores were drawn to the area and it has become a shopping destination.
Read more launchWatch highlights and course previews from previous years.
Read what other athletes have to say about their experience at the Boots and Brews 5K.
Be the first to share your experience with the community!
Spotted an error or missing detail about the Boots and Brews 5K? Help us improve.
Explore other exciting events happening in this same region.
location_on Freeport, Maine, US
calendar_today Sep 27, 2026
location_on Brunswick, Maine, US
calendar_today Sep 27, 2026
location_on Portland, Maine, US
calendar_today Sep 22, 2026
Hand-picked events we think you’ll love.
Sep 26, 2026
The 3 Beach Minimum Half Marathon is a spectacular run that starts at expansive Nantasket Beach, then follows the coast…
Read more
Nov 26, 2026
Our 6th Annual Tradition! Thanksgiving Morning @ 8am with the sun rising over the water. It does not get any better tha…
Read more
Nov 07, 2026
Shake it before the Marathon! The course is in Flushing Meadow Corona Park, right next to the iconic Unisphere. The cou…
Read more
Sep 26, 2026
The seldom seen Freedom Tunnel will echo with the sound of your feet as you run over it and through NYC's quintessentia…
Read more
