Banner photo: Sunset on the Taconics by David Eberhart. Photo taken from Rockwell Rd on Mt. Greylock

River's Edge Cycling's final Berkshires to Boston Tour is a wonderful memory. We loved sharing this amazing route across Massachusetts with riders from across the country and around the world.

The Adventure Cycling Association, a non-profit organization whose mission is to inspire and empower people to travel by bicycle, will present the tour in 2019. Visit for updates.

 The Tour begins at one of New England's most charming historic landscapes, Hancock Shaker Village in Hancock, Massachusetts

The Tour begins at one of New England's most charming historic landscapes, Hancock Shaker Village in Hancock, Massachusetts

The Berkshires to Boston Bicycle Tour is a four-day, 240 mile bike tour crossing Massachusetts from the New York border to downtown Boston. Showcasing the best of Massachusetts cycling, the tour begins in the scenic Berkshire hills, meanders through the Connecticut River Valley, rolls over the state's central plateau and spins through Lexington and other historic communities before arriving in the vibrant capital - Boston. There, riders join more than 5,000 cycling enthusiasts for TD Bank Hub on Wheels, Boston's annual bicycling festival. 

Now if you could only see
I know you would agree
There ain’t nowhere else to be
Like Massachusetts

— Arlo Guthrie, Massachusetts

Massachusetts is blessed with some of the finest road cycling in America and the Berkshires to Boston tour explores the best of the best. We kick off the tour with an optional Wednesday Warm-Up day exploring some of the Berkshires' great cycling routes. Choose a casual twenty-three mile loop that slips into New York (for those who want to grab the state line) and passes through one of the area's most-charming, small communities, West Stockbridge, before returning to Hancock Shaker Village along scenic back roads.  Or, choose a challenging forty-four mile ride up the state's highest peak, Mt. Greylock.  Or, just spend the day visiting our host site, Hancock Shaker Village - your entrance pass is included in your tour registration.

Our route across Massachusetts intersects with four of the state's designated scenic byways, recognized for their scenic quality, low traffic volumes and interesting experiences around every bend.  As we approach Boston, we take advantage of the metro area's wonderful bike paths like the Minuteman Bikeway, "America's Revolutionary Rail Trail" and the ever-expanding network of bike lanes and pathways encouraging visitors to explore greater Boston by bicycle.  

See Boston Magazine's December 2017 story about the tour by clicking on the image to the right:

Early autumn is the ideal time for this cross-state tour.  Cool nights are prompting an emerging pallet of fall colors but summer-like days offer perfect riding temperatures.

Experience the real Massachusetts.  Experience Massachusetts by bicycle on the Berkshires to Boston Bicycle Tour.

The Berkshires to Boston Sunset Tour

2018 will be the fifth and final Berkshires to Boston Tour presented by River's Edge Cycling.   Exciting changes in our lives (our expanding menu of tours and events, grand kids, and Reen's retirement) require that we redirect our energies in 2019 and beyond.  If the Berkshires to Boston Tour is on your bucket list, fill the bucket in 2018!  We already have riders registered from 16 US states and as far away as Australia.  Register today.

 The Tour concludes with TD Hub On Wheels, Boston's annual cycling festival.

The Tour concludes with TD Hub On Wheels, Boston's annual cycling festival.



In our Rider's words

“Thanks for an awesome trip.  For me it was the first time I rode 60 or 77 miles or rode through city traffic (which was actually much scarier than those hills!).

Amazing place to bike.  And thanks again to your staff who were outstanding! “ Rebecca McGrath, 2018

"Not just a ride, a social-community-building event." Steve Miller, 2016

"Fantastic route, great people, lots of support - it felt like summer camp for grownups on bikes!" Jeremy and Vanessa Berse, 2015

"I had a fantastic time every mile of the way and every minute at camp with a great group of riders. Thanks for the ride of my life!!!" Peter Garcia, 2015

"I couldn't have asked for a better experience on my first, multi-day bike tour. I met so many great people and really enjoyed seeing the beautiful towns and countryside of Massachusetts. Jessica Lilley, 2015

"6 stars on a 5 star scale!!! What makes this tour unique is not the delicious food -breakfast, dinner, and all the yummy, creative snacks provided along the way including suitable gluten-free and vegetarian options - not the beautiful scenery, not the superb organization including well-marked, thoughtful routes, not Tony the travelling masseuse or Mike the bike mechanic, although all that is true and wonderful; but, what is most memorable is the friendly community created by River's Edge Cycling's hospitality, warmth, dedication and passion to insure that every rider has the best experience possible." Adee Knapp, 2015

"One heck of a ride - challenging terrain, great people, amazing descents. Somehow they found every newly-paved road in Massachusetts and put it in the route! But the people make it an amazing experience- the group was fantastic and fun to camp with. The weather was unbelievably good and River's Edge ran the tightest of ships. Will be back (hopefully with friends) next year!" Francesco Cardiello, 2014

"Excellent tour. Best supported tour I have been on! Jeff Roth, 2014

"I can't say enough about how great a trip this was. The River's Edge team was the most organized, friendly and supportive team ever!" Joy Mills, 2014

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 Exploring Massachusetts scenic byways in autumn.

Exploring Massachusetts scenic byways in autumn.

About the Tour

Learn more about the routes, the accommodations and the Berkshires to Boston Bicycle Tour experience.

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