The Valley Roundabout

Heading to western hilltowns along the beautiful Ashfield Road

Heading to western hilltowns along the beautiful Ashfield Road

Discover the beautiful Connecticut River Valley from the seat of your bicycle in July or September of 2020. We’ve combined some of our favorite rides to create a long weekend full of handlebar-view adventures traveling the scenic byways and quiet back roads to some of the Connecticut River valley’s vibrant and charming communities.  You’ll spend two nights in the valley’s cultural center, Northampton, MA and an additional two nights in Historic Deerfield, brimming with history and 18th century charm.

View from Mt. Sugarloaf

View from Mt. Sugarloaf

Beautiful Bicycling in the Connecticut River Valley


The Connecticut River Valley offer some of the best cycling in America and the Valley Roundabout Tour explores many of the regional cycling highlights. Four half-century days give you 200 miles of lovely riding along scenic byways, quiet back roads and peaceful bike paths. You’ll also roll through a few charming hilltowns like Ashfield and Colrain and stroll down the famous Bridge of Flowers in Shelburne Falls.  Monday’s Brooks, Books and Waterfalls includes views of six waterfalls, a visitor center describing the Connecticut River’s natural history and a really fun used bookstore with the slogan, “books you don’t need in a place you can’t find”.

And no bike tour would be complete without wonderful little cafes and restaurants to sip coffee, eat pie, dive into ice cream or devour fresh pastry. Elmer’s Store in Ashfield, West End Pub in Shelburne Falls, Lady Killigrew Cafe in Montague, Tandem Bagel in Easthampton and 2nd St. Bakery in Turners Falls are just a few of the delicious destinations you’ll pass during your tour.

Learn more about each of the Daily Rides

Downtown Northampton

Downtown Northampton

Two Nights in Vibrant Northampton, MA and two nights in Historic Deerfield, MA

The tour brings you to two of the Valley’s most-loved communities, Northampton and Deerfield.

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Northampton, MA, is one of New England’s most vibrant little cities. Our hotel, the Fairfield Inn is a short walk from Main Street’s wide array of cafes, shops and restaurants. It’s also just a few hundred yards from the bike paths that connect Northampton with miles of fantastic riding up and down the valley.

On Saturday, we’ll ride to Deerfield for two nights at the Deerfield Inn. The Inn sits at the center of “the Street” flanked with historic homes and buildings dating from the mid- 1700’s.

Your tour registration includes double occupancy hotel accommodations and breakfast and dinner each day. Single occupancy rooms are available with payment of the single occupancy supplement.

Pricing and Registration

$989 Per Person (double occupancy)

$430 Single Supplement

Your Valley Roundabout Tour registration includes:

Misty Montague Riding

Misty Montague Riding

  • 2 nights double occupancy lodging at the Fairfield Inn, Northampton (Thursday and Friday).

  • 2 nights double occupancy lodging at the Deerfield Inn, Deerfield ( Saturday and Sunday)

  • 4 evening dinners ( Thursday through Sunday)

  • 4 breakfasts (Friday through Monday)

  • Luggage shuttle

  • Rest stops each day.

  • SAG support each day.

  • Marked routes, maps, GPS files and cue sheets for four valley bicycle tours.