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More cycling events nearby

  • Distance: 30.8 km from Whitingham
    Sun, Aug 02, 2026 at 8:00 AM

    The Greenfield Triathlon is the longest running triathlon in New England!

    Situated in the heart of Franklin County, the Greenfield Triathlon course meanders through the picturesque back roads of Greenfield, passes through the Historic Eunice Williams Covered Bridge, and features swimming in our very own Green River.

    Offering both International and Sprint distances for individual athletes as well as two- and three-person teams, the Greenfield Triathlon is great for both beginners and seasoned triathletes. A triathlon training program is offered Sundays leading up to the event. In Greenfield, our motto is “To Finish Is To Win!”

    All race proceeds benefit the Greenfield Recreation Department. The Greenfield Triathlon has raised thousands of dollars to support programs and events for families within our community. We thank you for your continued support.

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    17 Miles38 MilesRunSwimTriathlon via RunSignup
  • Distance: 45.9 km from Whitingham
    Fri, Aug 07, 2026 at 9:00 AM

    Hoopla 2026 dates just announced!

    Join us for a weekend of bringing folks together to enjoy cycling, camping, outdoor adventure and fun! Make new friends, ride awesome trails and try out new bikes. We have planned a family friendly event and are ready to inspire new riders as well as to challenge trail and road warriors alike. Enjoy guided rides for all levels in the beauty of the Berkshire Hills: road ride, single track, gravel, kids, enduro, double track and family friendly trails. Bonfires, food trucks, live music, BBQ and maybe even a disco tent! This is not a mountain bike specific event, it’s open to all disciplines of cycling whether you are on a road, gravel, kids, fat or mountain bike. Just c’mon out and play!

    Camping and event activities are located at Ponderosa Pines Campground at 50 Potter Mountain Rd, in Lanesborough. It is best accessed from the east or south(Pecks Rd, Bull Hill Rd or Churchill St and beware of your GPS advising you to come in from NY to the west via Potter Mtn Rd, you won’t make it over! The campground is nestled in-between Balance Rock State Park and Pittsfield State Forest(https://www.mass.gov/locations/pittsfield-state-forest), the 3rd and 4th largest public lands in the state of Massachusetts. Being on a dirt road it is the perfect location to start a gravel ride, with direct access to single track out the back of the campground is doesn’t get much better for the mountain bikers and the Mount Greylock Visitor Center(https://www.mass.gov/locations/mount-greylock-state-reservation) on Rockwell Rd is a short 7 miles away so you won’t use up to much energy before pedaling to the highest point in Massachusetts on your road bike! We will have a kids loop that stays close to

    the event site, but even young teenagers will find that the access to the single track is quite manageable.

    Our goal is to create a safe and fun environment to gather like minded people. With your participation, Hoopla is able to support other local cycling events, maintain and improve existing trails, purchase equipment for trail builders and donate to fitness/sporting organizations that need a little help.

    Hope to see you there!

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    CyclingEnduroGravelMountain BikingTrail via BikeReg
  • Distance: 29 km from Whitingham
    Sat, Aug 08, 2026 at 11:30 AM

    Next in the Pedal2Pints Social PopUp ride series!

    Revisiting the easy, scenic, classic route between two of the newer P2P-supporter breweries. We will start in Greenfield near Four Phantoms Brewing; head North to Bernardston (approx 6 miles) for a beverage (beer, seltzer, and NA available) at Incandescent Brewing; then return to Four Phantoms (approx 8.5miles) for more merriment (beer, mead, ciders, NAs all available) and snacks.

    Registration includes 1 beverage at each brewery and a food item back at Four Phantoms.

    Additional food and beverages available a la carte.

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    Cycling via BikeReg
  • 3871 Vermont Rte 7a, Shaftsbury, Vermont, 05262, United States
    OpenStreetMap Google Maps
    Distance: 36.1 km from Whitingham
    Sun, Aug 09, 2026 at 8:00 AM

    The Bike Hub is proud to announce our Sunday Epic ride series! These are all-day rides featuring some of the best mixed-terrain riding the tri-state area has to offer. Forgotten woods roads, fast gravel, rugged singletrack, and even a bit of hike-a-bike. These rides will be long, difficult, and absolutely beautiful. While there is no perfect bike for a Sunday Epic, anything with around a 2 inch tire will work. More details on terrain will be included in each event post. Sunday Epic's will be held the third Sunday of every month from April-September. Start location may vary, but will usually end will some sort of food and drink situation. Wheels down at 8am always.

    This one is gonna be extra tough. Bring a mountain bike of some sort, curly bars may not get you far. My goal here was to put together a ride with the toughest possible terrain and most amount of climbing in the least mileage. Enter the Grass Mtn Sufferset. If you've never visited this area you are in for a treat. Starts and ends at the Shaftsbury Historical Society on 7A, park by the red barn.

    A few notes on the nitty-gritty of these rides.

    • Sunday Epic's are fully self supported. Bring everything you need to successfully finish the route. We expect you to carry basics like spare tube, pump, multi-tool, patch kit, food and water, etc. Although we occasionally stop at a convenience store, there are many times where the ride is too remote for that to be an option.

    • We generally try to ride together, but you are welcome to do your own thing as long as you have the route. Group pace usually hovers somewhere around the 10mph average mark, but may be slower depending on terrain/climbing.

    • Expect this to take a good chunk of the day. Occasional stops for snacks etc. We move pretty continuously, but also aren't in a rush.

    RideWithGPS link here.

    Note that we don't charge anything for these rides, but we do welcome donations! We are a community-based 501c3 nonprofit focused on removing barriers to cycling for all within the tri-state area. We provide education, free access to bikes and cycling accessories, and provide a place for people of all ages and abilities to connect through cycling. For more info on our shop and programs, click here. Thanks!

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    CyclingGravelMountain Biking via BikeReg
  • Distance: 25.5 km from Whitingham
    Sun, Aug 16, 2026 at 8:00 AM

    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!

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    CyclingGravel via BikeReg
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