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New England Cycling: European Charm & Culture Close to Home

Embrace adventure and beauty in Maine, Vermont, Massachusetts, and more.

New England’s reputation for idyllic countryside precedes itself. Many Americans are adamant they will visit to witness the vibrant fall colors someday or explore the iconic small towns with their church steeples visible across the valleys. However, instead of traveling to New England, many of us put it off, finding ourselves drawn across the Atlantic to Ireland, France, or Italy to explore Europe’s historic villages and culinary delights. Yet there is much beauty, culture, and history to explore on our own doorstep, on any of our New England bike tours.

The turmoil of the past year has kept people stuck at home, yearning for adventure with no way to travel to other parts of the world. Well, Ciclismo Classico has spent over thirty years as a boutique bicycle tour operator in Europe and we believe very strongly that New England has so much of the charm and culture of Europe, only much closer to home, and we’d like to feed your curiosity and your sense of adventure.

ew England Cycling: European Charm & Culture Close to Home

This guide has been designed to help you choose which part of New England to explore by bicycle, but if you’d like to skip this step and have a conversation instead, you can schedule a call with one of our consultants or fill out the form below to receive some exclusive email guides to cycling in New England. Otherwise, keep reading; your next adventure begins as soon as you start dreaming…

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Maine Bike Tours – Pedal the shore of Penobscot Bay

Maine’s extraordinary scenery and hearty seafood dishes fuel body and soul

 

Three cyclists in colorful gear stand and sit by their bikes on a grassy area near a lake, with trees and hills in the background—capturing the spirit of adventurous cycling tours.
Three cyclists ride on a paved road beside a lake and trees, enjoying what feels like scenic bike tours. A sign on the right reads “Barrett’s Cove, Picnic Area, Swimming.” The sky is partly cloudy.
Maine is a state inextricably connected to the sea. Much of its history, economy, and way of life is connected to the ocean and it’s the ocean views that brings us back there year after year. Cycling is the best way to take in Maine’s sleepy seaside towns and lush countryside — smell the fresh sea breeze, gaze out at the iconic rugged coastline, and sample the traditional and contemporary seafood that puts Maine on the map for foodies all around the world. Find out more about our

Massachusetts Cycling Tours – The Berkshires, Deerfield, & Martha’s Vineyard

Explore picturesque historic towns, forested hills, and island shores

 

A cyclist rides through North Square, a small urban plaza surrounded by historic brick buildings and shops, enjoying one of the area’s scenic bike tours on a sunny day.
A person enjoys a scenic bike tour, riding along a leafy path bordered by brick buildings on a sunny day, with a tall glass skyscraper towering in the background.
Home to the first European settlements and the dramatic start of the Revolutionary War, Massachusetts is steeped in history. From the tree-shaded lanes and backwoods around Deerfield to the gentle landscapes and historic towns of the Berkshires, Massachusetts is an incredible state for cyclists who are keen to delve into some of the oldest towns and most beautiful cycling routes in the US. Massachusetts has one more ace up its sleeve: Martha’s Vineyard, perhaps America’s most beloved island. Discover history and live in the present on any of our lovingly crafted boutique Massachusetts cycling tours.

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Cycling in New Hampshire – Rolling hills, idyllic wineries, and historic architecture

Discover the quaint villages, cool forests, and deep history of the Monadnock Region

 

Six people sit on a grassy bank by a calm lake, facing the water and autumn trees, enjoying a peaceful break under partly cloudy skies—an ideal spot often found on scenic bike tours.
Six cyclists pose with their bikes on a paved road beside a large lake, surrounded by forested hills and clear skies—capturing the spirit of scenic bike tours in Italy.
Ciclismo Classico has run cycling tours all across Europe and we have always maintained that New Hampshire captures more than a little of Europe’s charm and sense of history. Cycling is the best way to explore the area’s rich landscapes, with outdoor cafés, quaint villages, and tiny wineries perfectly punctuating your journey. This cycling trip is extra special, as you will join Ciclismo Classico’s founder, Lauren Hefferon, as she guides you through her hometown. The incredible landscapes of New Hampshire inspired Lauren’s passion for cycling and are very much responsible for our ethos as we create boutique cycling tours all around the world. Find out more about our cycling tour in New Hampshire.

 

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Bike Tours of Vermont — Rolling hills, picturesque villages, and sublime lake views

A picture-perfect, pedal-powered adventure through the ”Ireland of America”

 

ew England Cycling: European Charm & Culture Close to Home
Four cyclists ride on a rural road past green fields, a farmhouse, and a red barn under a clear blue sky, capturing the spirit of international bike tours.
For boutique bike tours, Vermont is perhaps the most sought-after location in the US. Its rolling hills, verdant countryside, and quaint villages highlight why it is sometimes called the “Ireland of America”. Vermont certainly isn’t flat! So expect to cycle a few moderate hills on your journey. But also expect to be generously rewarded for each climb, with some of the most breathtaking views in all of New England. Vermont’s reputation often sells itself, but the truth is that it’s even better than the hype would have you believe. A bike tour of Vermont is the best way to fully experience its charm and beauty.

Enjoy New England!

Lauren Hefferon

Founder and Director

Your New England Cycling Odyssey Begins Here

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