Skip to main content

The Retreat Farm Ramble is a cycling and gravel event held on Sunday, August 16, 2026. It is located at 45 Farmhouse Sq in Brattleboro, Vermont.

Date:
Sun, Aug 16, 2026 at 8:00 AM
Location:
45 Farmhouse Sq
Brattleboro, Vermont
05301
United States
OpenStreetMap Google Maps
Links:
retreatfarm.org Register at bikereg.com
Tags:
Cycling Gravel

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!

More cycling events nearby

  • 44th Annual Lake Wyola Road Race [facebook.com] [Register at raceroster.com]

    Sun, Jun 14, 2026 at 9:30 AM

    Courses:

    This scenic 4.8 mile road race and walk start at the Lake Wyola Association Hall on Shore Drive and runs counter clockwise around the lake on mostly tree-canopied country roads. The first

    half of the course is paved with a challenging uphill climb. The second half is dirt roads with a small bit of pavement at the finish line and is mostly downhill with a flat finish.

    The fun run, a 1.5-mile run and walk, is an out-and-back course along Lakeview Road and Wendell Road with a short climb about a half mile in. The course starts and ends on pavement with about a mile on dirt/gravel road.

    Comments on the Race:

    "Probably the best road race under five miles I have ever seen.” John Stifler, running columnist, Daily Hampshire Gazette

    Bring the family to enjoy a day at the beautiful beach and picnic area at Lake Wyola State Park.

    Free post-race refreshments for all runners and walkers.

    Start Times:

    Walk 9:30am

    Run 10am

    Fun Run 10:10am

    Race Day Registration:

    On site reg will be available starting at 8:30am on race morning.

    Event Questions:

    Please email Maura at [email protected] with event questions.

    43 km from Brattleboro
    6 Shore Drive, Franklin County, Massachusetts, United States
    OpenStreetMap Google Maps

    Fun Run Gravel Hill Climb Road Run

  • The BIKES FIGHT CANCER Charity Ride [bikesfightcancer.org] [Register at bikereg.com]

    Sat, Jun 20, 2026 at 11:59 PM

    Love Bikes, Hate Cancer? We have a bike ride for you!

    The BIKES FIGHT CANCER Charity Ride

    Presented by PDC Incorporated

    June 20th 2026

    Tree House Brewing

    1 Community Place

    South Deerfield, MA 01373

    Overview:

    This charity FUNdraising bike ride, in Western Mass, supports families dealing with the burden of a cancer diagnosis and cancer research. Choose from 25 mile and 50 mile routes, that weave through the beautiful Pioneer Valley and along the Connecticut River with some nice long straightaways along green farm land and rollers with views of the river. The 50-mile ride will be a bit more challenging but will reward riders with great views! After the ride there will be lunch, refreshments and festivities.

    100% of rider donations will be used for cancer research and to support local families dealing with the burden of a cancer diagnosis.

    This is a can’t miss bike ride. We love bikes and hate cancer.

    What is included:

    • Choose from the 25 or 50 mile rides, that are fully supported, with awesome water stops, and facilities!

    • Bikes Fight Cancer Socks!

    • Post ride meal!

    • One Tree House Beer included!

    • Fundraising Goal of $100 - Reaching this goal will earn you a free Bikes Fight Cancer T-Shirt!

    Routes:

    • 50 Mile Route - Traditional, with some dirt roads (2.5 miles) - 8:00am start - 1950 feet of elevation

    • 50 Mile Route - Pavement Only - 8:30am start - 1900 feet of elevation

    • 25 Mile Route - 9:30am start - 850 feet of elevation

    The official route maps will be emailed to registered riders in early June.

    Notes:

    Helmets are required

    Rain or shine

    E-bikes are welcome

    No bike trailers please

    Bikes Fight Cancer's Mission:

    Use our love of bikes to raise valuable funds for cancer research and to support local families dealing with the burden of a cancer diagnosis.

    http://www.bikesfightcancer.org

    If you are looking to donate to a rider go here: https://www.pledgereg.com/bfc

    We are also hosting a free Intro To Group Riding Clinic in partnership with MassBike and Northampton Bicycle on May 17th. You can sign up for that here: https://www.massbike.org/75982/bikes_fight_cancer_intro_to_group_riding

    Any other questions email: [email protected]

    43.2 km from Brattleboro
    1 Community Pl, Deerfield, Massachusetts, 01373, United States
    OpenStreetMap Google Maps

    Cycling Trail

  • Endless Mountains Adventure Race [endlessmountainsar.com] [Register at runsignup.com]

    Mon, Jun 22, 2026 at 10:00 AM

    Now in its fourth edition, the 2026 Endless Mountains Adventure Race is returning to its roots as a five-day non-stop expedition race. This year's race will be headquartered out of North Adams, MA,

    and the course will take you on an entirely new journey of southern Vermont. Over those five days, teams will get to explore rolling mountains, lush forests, majestic waterways, iconic gravel, and twisty single track on a course that calls to mind the Untamed New England expeditions of years past and pairs it with the classic Rootstock flair that you have come to expect from Endless.

    Endless Mountains is the setting to challenge veteran adventure racers and offer an accessible entry point to those eager to take on their first expedition race. Teams of 2-4 will journey across some of New England's best adventure-land. Along the way, they will be called upon to work together to meet the challenges that only expedition racing can offer – challenging overland navigation, wild terrain, sleepmonsters, and weather that can tame even the most hardened outdoor enthusiasts. It is in those moments where the best stories are written!

    47.5 km from Brattleboro
    375 Church St, North Adams, Massachusetts, 01247, United States
    OpenStreetMap Google Maps

    500k Gravel

  • Pedal For Pups: A Fundraiser for the Franklin County Regional Dog Shelter [bikereg.com]

    Sat, Jun 27, 2026 at 9:00 AM

    30.3 km from Brattleboro
    56 1st St, Montague, Massachusetts, 01376, United States
    OpenStreetMap Google Maps

    Cycling

  • Tour De Glaze- Uphill Mountain Bike Race [stratton.com] [Register at bikereg.com]

    Sat, Jul 18, 2026 at 8:30 AM

    37.3 km from Brattleboro
    5 Village Lodge Rd, Stratton, Vermont, 05155, United States
    OpenStreetMap Google Maps

    Cycling Mountain Biking

More cycling events nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local events.