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
90 days remaining
$40.00
May 16, 2026
Distance — 3.1 Miles
Type — Running
90 days remaining
$40.00
May 16, 2026
Distance — 3.1 Miles
Type — Running
90 days remaining
$40.00
May 16, 2026
Distance — 0.5 Miles
Type — Running
90 days remaining
$8.00
May 16, 2026
Distance — Fun Run Boots and Brews (no BBQ)
Type — Running
90 days remaining
$5.00
May 16, 2026
Distance — Non-Runner BBQ (under 21)
Type — Running
90 days remaining
$5.00
May 16, 2026
Distance — Non-Runner BBQ 21+
Type — Running
90 days remaining
$15.00
These values represent the 3-year monthly averages for May in 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.
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