Skip to main content

More cycling events nearby

  • Distance: 41.7 km from Chatham
    Sat, Jul 25, 2026 at 7:30 AM

    START / FINISH LOCATION:

    Shire Breu-Hous

    63 Flansburg Ave

    Dalton, MA 01226

    The Mount Greylock Century presented by Berkshire Velo 413 features some of the most challenging climbs in western Massachusetts. Riders will be treated to quiet backcountry roads and some of the nicest views in the county. While the north side of Greylock and Kingsley Hill Rd have gained some notoriety, don't discount some of the lesser known climbs such as Monroe Hill, Windsor and East Hoosac. We recommend compact gearing as riders will encounter mid-teens and higher percent grades several times over the course of 12,000 feet of climbing. We believe the route ranks right up there amongst the most challenging centuries in the Northeast.

    Event details: Parking and registration are located at the Stationery Factory in Dalton Massachusetts. The Century riders will have a group start at 7:30 AM and Metric Century will start at their own-will at 9:30 AM. We recommend riders budget an additional two hours over their normal century pace. There will be five aid stations located along the route. The ride will be supported until ~4:30 PM.

    Post ride: The Shire Tavern will be opening the kitchen for us at 3:30 offering a full menu. Beers will be complimentary using fare tickets. A nice way to recover a bit before that drive home!

    Century and Metric Century Routes

    Last minute updates will be posted on our Facebook Page http://www.facebook.com/BerkshireVelo/

    The will be held, rain or shine!

    Warning: This is a difficult ride. Slower riders should opt for the Metric Century. You will be abandoned if you are out on the road past 5pm. Its not fair to volunteers who will be committing 12 hours of their time to support the ride only to have super slow riders still out on the road until dark.

    See full details
    12kCyclingGran Fondo via BikeReg
  • Distance: 31.8 km from Chatham
    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!

    See full details
    CyclingEnduroGravelMountain BikingTrail via BikeReg
  • 20 Tompkins St, Tannersville, Ny, 12485, Tannersville, New York, 12485, United States
    OpenStreetMap Google Maps
    Distance: 46.8 km from Chatham
    Sat, Aug 08, 2026 at 9:00 AM

    [8afa50cd-4e69-4c54-9e34-68040228009a.png]

    19th Annual

    Saturday, August 8, 2026

    Tannersville, NY

    REGISTER TODAY!

    Enjoy a challenging weekend of cycling in the Catskill Mountains of New York State

    with

    [Last Chance.jpg]

    THE 2026 TOUR OF THE CATSKILLS

    One-day gran fondo

    27, 52, and 74 mile distances

    Virtual Ride with GPS timing

    ALL PARTICIPANTS RECEIVE

    Professional mechanical and SAG support

    Motorcycle support

    Police support at selected intersections

    Stocked rest stops

    Full course signage and markings

    Catskills scenery and hospitality

    Register by July 25 and receive personalized bib numbers

    Event T-shirt guaranteed if registered by July 25

    Other event swag coming soon!

    SCHEDULE

    Friday, August 7

    • Early Check-in | 6-8 PM | Last Chance Antiques and Cafe - 6009 Main Street, Tannersville

    Saturday, August 8

    • Rider Check-in | 8-10:30 AM | Tannersville Municipal Parking Lot, 20 Tomkins Ave.

    • Open - 74 mile | 9 AM

    • Open - 52 mile | 10 AM

    • Open - 27 mile | 11 AM

    • Post-Tour After Party | 1-4 PM | Last Chance Antiques and Cafe - 6009 Main Street, Tannersville with Roadhouse.

    • Riders may start any distance anytime after 9:00 AM but may not receive support on the road outside of the above start times.

    • E-bikes welcome!

    RULES

    • This is a non-competitive recreational ride, not a race

    • All riders must obey all traffic control signage and signals (stop signs etc)

    • Riders must stay to the right of the road or on the shoulder at all times

    RIDE TIMING

    Each ride is self-timed - register on the Ride with GPS event page to have your time recorded!

    PARKING

    Upper Lake Road, Tannersville only (5 min walk, 2 min ride from start/registration). Do not park at the municipal parking lot / registration area!

    74 MILE COURSE

    74.1 miles / 120 km

    5593 ft of climbing

    Includes the infamous Devil's Kitchen Climb

    Max grade 22%

    39x27 gearing recommended

    4 Aid Stations + Water Zone at top of Devil's Kitchen Climb

    52 MILE COURSE

    52 miles / 84 km

    3750 ft of climbing

    Max grade 18%

    39x27 gearing recommended

    2 Aid Stations / Rest Stops

    27 MILE COURSE

    27 miles / 43 km

    2218 ft of climbing

    Max grade 12%

    39x27 gearing recommended

    1 Aid Station / Rest Stop

    Interested in sponsorship?

    Contact us today!

    [Anthem Sports Tours.jpg]

    #Global #Cycling #Adventures

    www.anthemsportstours.com

    CONTACT US TODAY!

    Join us for #Adventure

    About

    Anthem Sports Tours is a division of Anthem Sports of Greenville, SC. Founded in 2005, Anthem Sports has identified untapped, yet rapidly growing & tourism-friendly regions with the scenery and infrastructure that would be attractive to cycling tourists and travelers worldwide.

    Contact:

    [email protected]

    +1 719.428.5807

    full size image

    See full details
    CyclingGran FondoVirtual via BikeReg
  • Distance: 31.8 km from Chatham
    Sat, Aug 15, 2026 at 8:00 AM

    SWIM: 0.5mi | BIKE: 18mi | RUN: 3mi

    Crystal Cove | Old Route 66, Averill Park, NY

    The Crystal Lake Triathlon Race is a USAT Sanctioned Sprint Distance Triathlon in Averill Park, NY on Crystal Lake. The race is one of the most scenic races in the area. The race begins at the Crystal Cove beach and features a single loop swim. Transitioning into the bike leg of our race where racers set out on a gorgeous out and back bike course that passes through the beautiful countryside of Rensselaer County. Finally, the racers finish on a mostly flat run course around Crystal Lake.

    All participants will be required to either show USAT membership or purchase a one-day license and sign a USAT waiver.

    Event Registration Website: cdtriclub.org/index.php/race/

    Participation Type:

    • Individual (not part of a Team) Adult , Youth

    • Join a Team Adult , Youth -

    • *Aquabike Adult, Youth

    *The Aquabike race covers the same swim & bike courses as the Triathlon but will end when participants enter the Transition Area upon completion of the bike.

    See full details
    21.5 MilesAquabikeCyclingRunSwimTriathlon via RunSignup
  • Distance: 39.5 km from Chatham
    Sun, Sep 06, 2026 at 8:00 AM
    CyclingMountain Biking via BikeReg
More cycling events nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local events.