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 Hudson Valley’s 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:
Bartlett’s Orchard
Pittsfield, MassachusettsOctober 12 SCHEDULE:
8:15am: Check-in Opens
9am: Gran Fondo Departs (Distance: 55-62 miles)
9:30am: Medio Fondo Departs (Distance: 39-49 miles)
10am: Piccolo Fondo Departs (Distance: 28-32 miles)
10:15am: Ramble Ride Departs (Distance: 12-15 miles)
11:30am-5pm: Post-Ride Barbecue and Celebration
First-Class Upgrades Available
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Distance: 55-62 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!
See a sample route below.
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Distance: 39-49 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.
See a sample route below.
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Distance: 28-32 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.
See a sample route below.
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Distance: 12-15 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.
See a sample route below.
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Join us the night before the Fondo 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.
More information about this year's menu and farm partners coming soon.
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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 Fondo event
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 : Warm-Up Ride
Meeting Location: Stockbridge Town Park to Tanglewood.DAY 2: Meet the Farmers
Meeting Location: Jiminy Peak
Farm Stops/Experiences:
Stop at Shadowbrook Farm to tour the farm and learn about the local farming practices
Your Guide:
Your weekend adventure will be led by former pro-cyclist Tyler Wren, along with experienced lead bike guide(s) and a dedicated SAG support team. Together, they’ll ensure a seamless, enjoyable, and unforgettable experience every step of the way.
GO PRIVATE-Private pre-fondo cycle tours plus Sunday event and Farm Benefit dinner is available upon request
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· Bartletts Orchard
· Hilltop Orchards
· No.6 Depot Roastery & Café
· Turn Park Sculpture Gardens
· Highlawn Farms Dairy
Sample Routes:
Our official 2025 routes will replace these sample rides closer to the event date. Check for updates.