The Berkshires: Pioneer Valley Paradise
The Gentle Landscapes, Farms and Historic Towns of the Berkshires
Download a Detailed Itinerary
Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:
- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
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The Connecticut River Valley is what’s left of North America’s sixth great lake, the 200 mile long Glacial Lake Hitchcock. With Northampton at the valley center, this terrain is flat to rolling farmland, with forested hills as you climb out of the valley. Northampton is a destination city, with many food options, museums, shops, and five breweries on the rail trail. Northampton also has active farms and thousands of acres of conservation land within the city limits. All of the riding surfaces on this tour are paved and are fine for road bikes. There is a long history of bicycling and bike culture in Northampton. Northampton also has a long history of progressivism, and was home to Black abolitionists Sojourner Truth and Frederick Douglass in the utopian village of Florence.
Tour Essence
- Ride on 700’ and 1600’ rail trail bridges across the Connecticut River
- Every ride will have daily tastings of award-winning cheeses, pasture-raised meats, artisanal bread, frozen yogurt, local ice cream, handmade pastries, heirloom ciders, and craft beers
- Safely exit and enter the city for the daily rides on the Northampton Rail Trail System, connecting nine towns with 27 miles of car-free paved rail trail
- Many ebike rental kiosks are in the area for quick exploring. Take a three-mile round trip to see the river at sunset from the Norwottuck bridge
- Northampton is the hometown of Calvin Coolidge: Governor, Vice President, and 30th US President
- Discover a thriving local food, culture and arts community in downtown Northampton.
- Savory Foodie Treasures included on this Exclusive Tour:
- Northampton Foodie Walking Tour and tastings to local specialty shops with passionate Foodie and owner of Pioneer Valley Food Tours Deborah Cristakos
- Visit with Jonathan Stevens at Hungry Ghost Bread in Northampton who sources much of his grain locally and also has its ground at a local mill.
- A beautiful stop and wine tasting at Glendale Ridge Vineyard, where guests taste a selection of locally made wines along with a picnic while gazing at the Mount Tom Range.
- A visit to the Thomas Farm and Dairy where Laurie and Jim have a herd of 80+ much-loved goats (each called by name) to make their delicious goat cheese, as well as several cows to make their cheddar cheese and gouda.
- A snack stop at the exclusively Red Fire Farm in Montague for a tour of their fields and to hear their story from farmer Ryan Voiland who started farming in his backyard at 10 years old! Organic to the core!
- A visit to the 2020 winner of the SBN (Sustainable Business Network) Sustainable Business award: The Barstow’s Dairy Farm and Store. Owned and operated by six and seven generations of the Barstow family, the farm provides the best possible care to their cows yielding healthier animals, better quality milk, higher milk yields, and reduced vet bills. Barstow’s uses rotational cropping, cover crops, and, in 2019, completed a four-year transition to becoming 100% no-till on their 450 acres of wide-open Massachusetts farmland.
- Read more about Why the Pioneer Valley in Western Massachusetts is the Perfect Foodie Destination
What to Expect
Terrain
RollingStart Location
Northampton, MAEnd Location
Northampton, MAMileage
Average Daily: 36 / 39.4 Total: 107.8 / 118.1Elevation
Average Daily: 874.6 / 1,395
2021
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Three Ciclismo Feast days
- 1 Lunch, 2 dinners
- Walking foodie tour with tastings
- Visits at 1 vineyard, 1 cider house, and 1 brewery
- Ciclismo Guides
- Van Support
- Snacks
- Ciclismo Classico Jersey
- Ciclismo Goodie Bag
- Welcome cocktail
Bring your own! Bikes are not included for this specific trip.
Call us if you need a rental bike!
- All breakfasts, 1 Lunch, 2 dinners
- All Accommodations (3 nights) at Hotel Northampton
- Ride on 700’ and 1600’ rail trail bridges across the Connecticut River
- Ride by land farmed continuously since 1660.
- Northampton Foodie Walking Tour with tastings at local specialty shops, all proud to source their ingredients regionally
Start Location
Northampton, MAFly Into
Bradley International Airport, Windsor Locks / Hartford CT (BDL)End Location
Northampton, MAFly Out Of
Bradley International Airport, Windsor Locks / Hartford CT (BDL)Vineyard Loop by the Mt Tom Range
Meals Provided
DinnerAverage Mileage
25,2 milesElevation Gain
945 feetRiding Terrain
Gentle RollingMeals Provided
DinnerAccommodations
The Hotel Northampton
The Hotel Northampton, built in 1927, is a proud member of Historic Hotels of America. With 106 newly renovated guest rooms and luxury suites, Hotel Northampton offers every guest a gracious hospitality, a quality service and an experience. We are conveniently located in the center city of Northampton, where all points of attraction are within walking distance. Experience the many great attractions like the Calvin Theater and Academy of Music for some their popular concerts and events.
Connecticut River Loop
Meals Provided
BreakfastAverage Mileage
26,5 / 44,6 milesElevation Gain
450 / 1150 feetRiding Terrain
Gentle RollingMeals Provided
BreakfastAccommodations
The Hotel Northampton
The Hotel Northampton, built in 1927, is a proud member of Historic Hotels of America. With 106 newly renovated guest rooms and luxury suites, Hotel Northampton offers every guest a gracious hospitality, a quality service and an experience. We are conveniently located in the center city of Northampton, where all points of attraction are within walking distance. Experience the many great attractions like the Calvin Theater and Academy of Music for some their popular concerts and events.
Beaver Dams and the Holyoke Range Loop
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
33,3 / 48,3 milesElevation Gain
1.235 / 2.100 feetRiding Terrain
Gentle RollingMeals Provided
Breakfast, Lunch, DinnerAccommodations
The Hotel Northampton
The Hotel Northampton, built in 1927, is a proud member of Historic Hotels of America. With 106 newly renovated guest rooms and luxury suites, Hotel Northampton offers every guest a gracious hospitality, a quality service and an experience. We are conveniently located in the center city of Northampton, where all points of attraction are within walking distance. Experience the many great attractions like the Calvin Theater and Academy of Music for some their popular concerts and events.
