Tour of the Hilltowns

A New England Classic Through the Hilltowns of the Berkshires


Spring 2021 NOTICE: Due to the ongoing COVID-19 pandemic, the 2021 edition Tour of the Hilltowns is canceled. We will try again in 2022.  We thank you for your continued support and hope 2021 gets us all back to “the old normal.”

The Tour of the Hilltowns is a classic New England road race. It features many amateur divisions and a more challenging professional field. The race goes through the Notchview Reservation in Windsor, MA. It includes the challenging Route 8A descent and the difficult East Hawley Road climb, which the pros ascend twice.

Registration Information:

  • Standard BikeReg fee applied to online registration.
  • Entry Fee includes NEBRA Rider Surcharge of $1 and USA Cycling Insurance Surcharge of $4.75
  • Day-of-race registration is $75 for all riders except Juniors, which remains $20.
  • Refund policy:
    • Full refunds until 6/1, no questions asked.
    • From 6/2 until close of preregistration, riders may transfer their entry to another rider themselves via Bikereg, or request a credit for next year’s race.
  • Held under USA Cycling event permit # .
  • All USA Cycling rules apply; approved helmets are mandatory; no mountain bikes, aero bars or straight bars.
  • There will be roll-out for any riders age 18 or younger immediately following their finish.
  • Races may be combined if less than 10 riders are pre-registered for any category.
  • USA Cycling license required. One-day licenses for Cat 5 Men and Women (now called Novice categories) may be purchased at registration for $10.
  • USA Cycling free race coupons are accepted.
  • Wheels in / Wheels out for all fields.
  • Bring your trainer to warm up; riders warming up on the local roads do so at their own risk.

Course Description: An 84.2 mile double loop with two major climbs and one feed zone for the P/1/2/3 category, and a 52.6 mile loop with one major climb and one feed zone for all other categories. Start is at Notchview Reservation on Rt. 9 in Windsor, MA. Finish is a short 6% climb at the top of Rte 8A in Windsor, about 1.5 miles from Notchview.

Volunteers Needed:  We need volunteers to help make a safe race. If a racer brings a volunteer, the racer’s entry fee is waived. E-mail in advance with the name of the racer and the volunteer.

Directions to Notchview Reservation: West on Route 9 from Northampton, MA, 29 miles to Windsor. Notchview Reservation is about one mile east of Windsor Center and Rt. 8A. Use 2241 Berkshire Trail, Windsor, MA for your GPS (Google Map). Parking is in the field prior to the entrance, look for signs. NO PARKING ALLOWED AT THE FINISH OR ANYWHERE ON RTE 8A. 

Area Attractions: The race location is less than a 30-minute drive to the Berkshires or the Pioneer Valley. Discover epic riding, hiking, swimming, zip-lines, paddling, shopping, dining and more.

  • Head west on Rte 9 to The Berkshires, featuring beautiful open farms, mountains, historic railroads, museums, small towns, hidden hiking and swimming gems, and more. Start with The Berkshires Website for discovery. The New York Times has a great article about 36 hours in the Berkshires.
  • Head east on Rte 9 to the Pioneer Valley, also featuring beautiful open farms, larger towns and cities, the Five College community, many wineries and breweries, but still plenty of hidden recreational opportunities and unique shopping and dining, notably in Northampton and Amherst.

Video Course Preview: