2 cycling, fun run, running, and other events in Brattleboro, Vermont
From big races to Saturday morning group runs—find cycling, fun run, running, and walking events and connect with the local endurance sports community.
Brattleboro
2 events in Brattleboro-
Sat, May 02, 2026 at 9:30 AMSee full details
Green Street School will be hosting the 14th Annual Tulip Trot 5K Fun Run/Walk on Saturday May 2nd at 10:00 A.M. This event is fun for all ages-- GSS Students can register for free prior to 5/1 at 5pm . We will also have a Sprout Sprint (3 laps around the school) for our younger kids (K-3)-- this race is FREE but you will still need to register your child (no charge).
This year we are excited to have North Star Timing back as our official timer for the event. North Star will provide electronic chip timing and super fast live results with its Mylaps BibTag Timing System, the same system used at the Boston Marathon.
Event Start Time:
Bib pick up and/or day of registration begins at 8:30 am for 5K only. The Sprout Sprint begins at 9:30am-- there is no bib pick up for this event so please just arrive 15 minutes prior to start time. The 5K race will start at 10am. We encourage you to sign up in advance for the 5K to save on registration fees and to make the morning of the race easier. A limited number of Tulip Trot shirts will be for sale the day of the event.
Pricing Information:
Early Bird Registration:
Now thru 4/1/26:
under 12 $0 (no charge)
13+ $20
Regular Registration:
4/2/26 thru 5/1/26 (5pm):
under 12 $0 (no charge)
13+ $25
Race Day Registration:
May 2, 2026 8:00 A.M.-9:30 A.M.
under 12 $15
13+ $30
*Registration for the Sprout Sprint (Grades K thru 3) is FREE but you will still need to register your child
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Sun, Aug 16, 2026 at 8:00 AMSee full details
The Retreat Farm Ramble is our third annual cycling event with multiple rides to choose from. This year we'll have a 33-mile mixed gravel and pavement farm tour and a 15 mile family-friendly hybrid bike and E-bike tour. Each route will have aid station stops and riders on the 33-mile route will also make stops at partnering farms to refuel on provided treats.
The ride will end at Retreat Farm, where our Farmhouse Square will be open with music, food, and tasty craft brews. We'll have food trucks, music, mechanical support, and a farm full of fun for the entire family, with hiking, a forest playground, and animals out on pasture. Our North Barn and Thirsty Goat Bar will be open, and you can visit the Retreat Farm Market featuring VT-made cheese and food products.
The first fifty riders to sign up will receive a complimentary Retreat Farm hat on the day of the event!