A TASTE OF THE berkshires
Nestled in the western part of Massachusetts, the Berkshires offers a stunning backdrop for cyclists. This region is known for its scenic farmland, rolling hills, and vibrant forests, with breathtaking views of the Taconic and Berkshire Mountains. Riders can immerse themselves in the Berkshires’ rich farm-to-table culture, enjoying fresh, local flavors while taking on a ride that combines natural beauty, physical challenge, and culinary delight. Whether you’re joining us for the Fondo alone or extending your stay for the full Weekend Getaway, this event offers something for every cyclist and food lover.
riding level
Our courses are designed to accommodate riders of all levels, from beginners to avid enthusiasts. The terrain in The Berkshires ranges from gentle hills to steeper climbs, offering a challenge that’s both invigorating and manageable.
Highlights
Main Event - The Fondo
Choose your adventure from one of four scenic distances, each thoughtfully designed to include farm stops featuring fresh, locally sourced snacks to fuel your ride.
Signature Farm Benefit Dinner
Kick off your weekend with a signature pre-Fondo gourmet dinner experience. This Farm to Fork benefit supports local farms and highlights the best of the region’s seasonal flavors.
Post-Ride BBQ
Celebrate your ride and your accomplishments with a lively post-ride barbecue. Enjoy delicious food, great company, and the vibrant energy for a ride well done.
Weekend Getaways
Take your Fondo experience to the next level with a three-day cycling adventure. Enjoy two days of pre-Fondo guided bike tours, exclusive behind-the-scenes farm visits, and tastings that immerse you in the Berkshires Region rich farm-to-table culture and vibrant local community.
THE fondo
Pick one of four distance options and enjoy stops at local farms to refuel with fresh, seasonal snacks, while supporting the area’s vibrant agricultural community.
gourmet Farm benefit dinner
Be part of our pre-Fondo experience with a three-course, sit-down dinner that supports local farms and community programs.
weekend getaway
Each day showcases a different aspect of what makes this region so unique, highlighting the culture, traditions, and farming practices of The Berkshires.
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LOCATION:
Hilltop Orchards: Home of Furnace Brook Winery, Berkshires508 Canaan Rd, Richmond, Massachusetts
October 12 SCHEDULE:
7:30 am: Check-in Opens
9:00 am: Gran Fondo Departs (Distance: 55-62 miles)
9:30am: Medio Fondo Departs (Distance: 35-45 miles)
10am: Piccolo Fondo Departs (Distance: 25-35 miles)
10:15am: Ramble Ride Departs (Distance: 12-20 miles)
11:30am-5pm: Post-Ride Barbecue and Celebration
First-Class Upgrades Available
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Distance: 50-62 miles
Our longest route features 4 farm-based aid stations.
Each stop provides a gourmet selection of seasonal, farm-sourced treats. You'll be fully supported mile after mile with downloadable turn-by-turn directions, color-coded route markings, and on-course mechanics.
Gran Fondo is the premier experience in The Berkshires—if you have the legs for it!
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Distance: 35-45 miles
Our most popular route features 3 farm-based aid stations.
Each stop provides a gourmet selection of seasonal, farm-sourced treats. You'll be fully supported mile after mile with downloadable turn-by-turn directions, color-coded route markings, and on-course mechanics.
Medio Fondo features the best roads and farms The Berkshires has to offer..
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Distance: 25-35 miles
Our most accessible route features 2 farm-based aid stations. Each stop provides a gourmet selection of seasonal, farm-sourced treats.
You'll be fully supported mile after mile with downloadable turn-by-turn directions, color-coded route markings, and on-course mechanics.
Piccolo Fondo offers a rewarding fitness goal as you tour The Berkshires and support farms along the way.
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Distance: 10-15 miles
Our introductory route features 1 farm-based aid station.
Your farm stop provides a gourmet selection of seasonal, farm-sourced treats. You'll be fully supported mile after mile with downloadable turn-by-turn directions, color-coded route markings, and on-course mechanics.
Ramble Ride offers equal access to The Berkshires—with fewer miles to pedal! Beginners and families with young kiddos, this is your ride.
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Join us the night before the Fondo Saturday 4 pm, October 11 for the Farm Benefit Dinner. Proceeds from ticket sales directly support our host community farms and programs.
The evening will feature a multi-course gourmet meal of seasonal, locally-grown food and cash bar. Guests can look forward to toasts from Farm to Fork's Partners and representatives from the farm community.
Our Farm Benefit Dinner Host will be Abbey at Once Upon a Table 36 Main St. in Stockbridge, MA. An intimate restaurant tucked away in the Mews area of downtown Stockbridge, the heart of the Berkshires. The menu is based on seasonal ingredients available from their local farm based suppliers. The menu changes often but we can look forward to delicious entrées, soup/salad & dessert.
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If you are planning to travel for the Fondo and are eager to see more of what makes the Berkshires special, spend the weekend with us!
The Weekend Getaway package is filled with additional experiences not explored on Fondo Day. You’ll enjoy:
Two days of guided bike tours plus the Gran or Medio Fondo Route (your choice)
Gourmet Pre-fondo Farm Benefit Dinner ticket
Entrance fees to experiences, farm stops, and lunches along our tour
A 2025 Artist's Collection Farm to Fork jersey, and more!
DAY 1 Friday: Two State Ride MA to NY 27 miles
Meet Time:0900 & Ride Start: 0930Meeting Location: Jiminy Peak Mountain Resort 37 Corey Rd, Hancock, MA 01237
Farm Stops/Experiences:
Stop at Shadowbrook Farm in Lebanon, NY to tour the farm and learn about the local farming practices. Have a snack at their Farm Stand, see the Pigs & Chickens roaming the fields & barns, or just play catch with their farm dog who is obsessed with his new ball toy.
After the ride, let’s enjoy a post-ride lunch & beverage in Pittsfield.
Day 2 Saturday: The Berkshires two Farm Favorite
We start & end or day at Picturesque High Lawn Farms at 535 Summer St, Lee, MA 01238
Start the morning off with a visit to the Calf Barn. Then end the days ride with an ice cream treat at their farmstand creamery.
Along the way we briefly visit Stockbridge, MA. A Berkshires Town first settled in 1734. It is home to the Norman Rockwell Museum & the Berkshire Botanical Gardens.
Along the route we will stop at Windy Hill Farm & Orchard to visit their diverse Horticultural operation . We can venture into the orchards to pick your own apples or berries, or peruse their Farm Store.
We will make a stop at Baldwin Farm to meet the Farmer, learn about the family history of healthy organic farming practiced for generations. We will enjoy lunch at their outside mobile food service kitchen.
Your Guide:
Your weekend adventure will be led by Warren Hamblet, and directed by Scott Molyneaux, Farm to Fork Owner, along with a dedicated SAG support team. Together, they’ll ensure a seamless, enjoyable, and unforgettable experience every step of the way.
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· Bartletts Orchard
· Hilltop Orchards
· Turn Park Sculpture Gardens
·Highlawn Farms Dairy
Stanton Home Farm
Windy Hill Farm & Orchard
Baldwin Farm
Final Routes:
Our official 2025 Berkshires Fondo routes are available NOW.