The Best of Massachusetts Cycling

The Berkshires to Boston Bicycle Tour introduces riders to the best of Massachusetts cycling - lots of peaceful roads, good pavement and magnificent scenery along with some fun, urban riding on bike paths, bike lanes and community streets. 

Scene from the Saddle

Wednesday: Wednesday Warm UP

The Berkshires offers some fantastic cycling and this year, we'll be offering a few alternatives to give tour riders the opportunity to explore the region before beginning the cross-state tour on Thursday.  

The Wednesday Warm Up "23" is a pretty twenty-three mile route from Hancock Shaker Village south to the small town of West Stockbridge.  Along the way, you'll slip into New York for a few miles before crossing back into Massachusetts.  Check out the Wednesday Warm Up 23 route at Ride With GPS.  West Stockbridge is a charming community and a good option for a lunch stop.  Visit the Shaker Dam Coffeehouse or the Six Depot Roastery for coffee, a snack or lunch before returning to Hancock Shaker Village.

Bicycling Magazine recently picked the ascent of Mt. Greylock, Massachusetts' highest peak, as one of America's best rides!  We're offering our riders the opportunity to experience this classic climb as an optional, supported pre-tour warm up. The Massachusetts state parks agency, MassParks, recently rebuilt the Mt. Greylock Scenic Byway across the mountain.  See the Wednesday Warm UP route at ride with GPS.  Stop by the information center on Rockwell Road to learn about the reservation and re-fuel at the event rest stop before riding to the peak.  The 8-mile climb offers a great workout and rewards you with gorgeous views of five states from the summit.  Enjoy lunch at Bascom Lodge on the summit before an invigorating descent back down Rockwell Road and returning to Hancock Shaker Village.  

The Berkshires offers great riding on quiet roadways and you're sure to find emerging fall colors, wonderful views and interesting shops and stops along the way.   Make the most of your time in the Berkshires by signing up for the Tuesday night camping option at HSV and you'll be ready to ride after a hearty breakfast on Wednesday morning.

Learn about our evening's activities at Hancock Shaker Village in the "Off The Bike" page.


Thursday - Hancock to Sunderland

Today, we begin our journey across Massachusetts.  Our first day's route covers just over 60 miles between Hancock Shaker Village and Sunderland, MA in the Connecticut River valley.  Most of the route follows one of Massachusetts' designated scenic byways, the Route 116 Scenic Byway.  See the Thursday route at Ride with GPS. Along the way, riders pass through Pittsfield, the Berkshires' largest city and spin along MassParks' Ashuwilticook Rail Trail with its great views of local lakes and the Mt. Greylock range.  Riders then climb 1,000 feet to the top of the Hoosac Range and the highest point along the entire tour  (2,006 feet above sea level) before rolling into the Savoy rest stop at about mile 25.  

There's lots of quiet roads, new blacktop and picturesque scenery over the next 20 miles as riders follow the scenic byway and roll to the next rest stop in the Town of Ashfield.  Ashfield's also a great spot for a lunch break at Elmer's Store or in one of the other small eateries in town.  

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From Ashfield, the tour steadily descends through Conway and into the flat Connecticut River Valley in South Deerfield.  Riders pass by Mt Sugarloaf State Reservation with its paved road to the summit.  If you haven't had enough riding so far today, take a short detour up the access road and catch one of the most-photographed views in the Valley before rolling over the Connecticut River bridge and into Sunderland and camp.  Or, take a walk over from camp before dinner to catch the great view. 

 

Learn more about Sunderland and the evening's plans at the "Off The Bike" page.


Friday - Sunderland To Devens

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Today is the longest day of the tour - 79 miles as we climb out the river valley and ride through the state's central plateau to Devens, MA.  See the Friday Route at Ride with GPS. The day begins with flat riding through the fertile farmlands along the Connecticut River before beginning a gradual 11-mile climb up to the Town of Wendell, and our first rest stop at the General Store, 1,000 feet higher than our Sunderland starting point. 

The next 40 miles feature quaint New England towns like Petersham and Princeton and a rolling route through the heart of Massachusetts.  Rest stops on the Barre Town Common and the Sterling Fire Station are good opportunites to get some snacks and water.  Barre is about halfway through the day and a good spot for lunch and connecting with fellow riders.

The final 20 miles are nearly all downhill or flat as riders drop over 1,000 feet to Devens.  You won't want to miss Kimball's Farm Ice Cream in Lancaster at mile 70.  Celebrate your accomplishment today with one of the biggest ice cream cones or dishes you've ever seen.


Saturday - Devens to Boston

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Today is the shortest and easiest day of the tour - less than 50 miles and a net loss of nearly 300 feet in elevation as we travel into Boston.  See the Saturday Route at Ride with GPS. All the more reason to take the time to experience the region and the ride as you travel into Boston. Revolutionary War history is evident all along this stretch as the route passes through the towns of Acton, Lexington and other communities with a rich 18th-century history.  You'll also want to savor the tastes!  Along the way, you'll find farm stands, orchards, bakeries and ice cream.  

Eleven miles of today's route follows the Minuteman Rail Trail, "America's Revolutionary Rail Trail".  This popular shared-use pathway through four suburban Boston communities offers a great route into the city.  We ask all riders to ride slowly and respectfully along these shared-use pathways.

While some choose to explore the history and attractions of today's route, others choose to get into Boston for the TD Bank Mayors Cup Criterium.  Now in its seventh year, the men's and women's bicycle races around Boston City Hall will feature nearly 200 top professional racers including Olympians and national champions who will compete for $30,000 in prize money.  This criterium is the final race of the USA Cycling national criterium calendar.  


Sunday - TD Bank Hub On Wheels

Today, riders will celebrate cycling with 5,000 friends who enjoy riding as much as they do. TD Hub on Wheels is Boston's annual cycling celebration and caps a weekend of cycling events in the city. Bicycles take over Storrow Drive and other roadways as riders explore Boston's parks, neighborhoods and beaches on routes ranging from 10 - 50 miles. 

Each year, Berkshires to Boston riders have led thousands of riders out of the start near City Hall.  We appreciate our partnership with Boston Bikes and look forward to participating in this annual cycling celebration in 2016.