The Heart of New Hampshire
The Charm and Beauty of Europe Close to Home
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The Charm of Europe Close to Home! Cycling in Southern New Hampshire is the closest you can get in the USA to the cultural vibe and cycling nirvana of Europe. Spin and enjoy historic architecture, cute outdoor cafes, tiny wineries, fascinating history, tiny villages, cobblestone pathways, covered bridges, abundant lakes, cool forests, zigzagging rivers, farmland, and magic moments galore! Join Ciclismo Founder Lauren Hefferon in her hometown and discover the rich history, pristine landscapes, and gorgeous backroads of the Monadnock Region that inspired her passion for bicycle travel. In every direction, the roads and hamlets along the way connect and lead us to stories of an era and people that formed the foundation of a highly independent and hardy culture determined to rebel from England and establish themselves as among the most self-reliant in America, thus the state’s motto, Live Free or Die. New Hampshirites take their role of protecting their land seriously maintaining some of the most intense conservation programs in the country. For four nights we stay in College town of Keene, the heart of the picture-perfect Monadnock region, known as NH’s cultural corner that is a perfect cycling base offering a variety of gorgeous loops for all cycling abilities and The National Trust for Historic Preservation has added Keene to its list of “America’s Dozen Distinctive Destinations,” calling it a “Currier & Ives landscape come to life.”Lauren has selected her favorite cycling loops from Keene that include a dive into the colonial and Native American past of North America. Each day you’ll experience mile after mile of gorgeous scenery and a glimpse into the connective tissue of our nation’s past. Pedal past and learn about the fascinating historic architecture, art galleries, covered bridges, abundant lakes, cool forests, zigzagging rivers, farmland galore, and daily views of the region’s jewel, Mount Monadnock, (Mountain That Stands Alone) the second most climbed mountain in the world. Known for its presence in the writings of Ralph Waldo Emerson and Henry David Thoreau, it is the most prominent mountain peak between the White Mountains of New Hampshire and the Massachusetts Berkshires. We are based for four nights in downtown Keene, a charming and eclectic mix of old-time shops, modern retailers, restaurants, and cool coffee shops. Recently Keene has added 15 stunning historical “Walldog” murals to its downtown landscape that beautifully depict the region’s historic resources and rich cultural heritage. Keene is framed by one of the most beautiful Main Streets in the world with the picturesque (and much-photographed) United Church of Christ at the top of Keene’s Central Square. For photography fans, Lauren will be stopping to show you all of the most photogenic hot spots and for the gravel hungry we have dedicated one day to recreate a mini Eroica experience.
Tour Essence
- Visits to the historic hamlets and mill towns of Harrisville, Dublin, Gilsum, Surry, Westmorland and West Chesterfield
- Walking tour of downtown Keene including the 13 historic murals with expert historian Allen Rumrill
- Rides along Lake Nubanusit, Silver Lake, Swanzey, Lake Spofford, and the winding Ashuelot and Connecticut rivers
- Pedal over and through the region’s abundant covered bridges and stone bridges
- Visit the Poocham Family Winery and the Walpole Mountain View Winery
- Visits to art galleries and craft shops
- Honey and Liqueur Tastings at Slovenia Beekeeping
- Visit Burdicks (famous) Chocolate Factory in Walpole, NH
- Daily tastings at gelato and farm stands
- A deep and fascinating dive into America’s colonial and Native American past
- The only Southern NH bike tour of its kind
- Hike up Mount Monadnock, the second most climbed mountain in the world (and you’ll find out why
- Led by Lauren Hefferon, native of Keene and Founder of Ciclismo Classico
- Women’s Only Weekend October 6 – 10! Learn More.
- Explore our Top Photos from our Southern New Hampshire Bike Tours
What to Expect
Terrain
Rolling and hillyStart Location
Keene, New HampshireEnd Location
Keene, New HampshireMileage
Average Daily: 29-45 Total: 115-200Elevation
Average Daily: 1500 feet Total: 5000 feet


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.
- Van support
- 2 experienced guides
Bring your own! Bikes are not included for this specific trip.
Call us if you need a rental bike!
- All accommodations
- All breakfasts
- 1 lunch
- 3 dinners
Start Location
Keene, New HampshireFly Into
Manchester, NHEnd Location
Keene, New HampshireFly Out Of
Manchester, NHSwanzey
Meals Provided
DinnerAverage Mileage
26.9 milesElevation Gain
962 ftRiding Terrain
Flat and rollingMeals Provided
DinnerAccommodations
Fairfield Inn & Suites
The Fairfield Inn & Suites Keene Downtown, located within a historic one-hundred-year-old building in the heart of downtown Keene, New Hampshire, invites you to relax in unique, boutique-like guest rooms. The Fairfield Inn & Suites Keene Downtown is a treasured gem overlooking Main Street and sits amongst area dining, shopping and artisans just footsteps from the hotel. Each of the uniquely styled guest rooms encompass the beauty and history of the century-old building while offering modern amenities such as free Wi-Fi, spacious work desks, crisp linens, pillow top mattresses and refrigerators. The Fairfield Inn & Suites Keene Downtown offers superior accommodations while providing the courteous service you deserve.
Surry-Walpole-Alstead
Meals Provided
Breakfast, DinnerAverage Mileage
23.9/50 milesElevation Gain
1,306/3,500 feetRiding Terrain
Rolling and hilly. Some gravel. Big climbs on the extra loopMeals Provided
Breakfast, DinnerAccommodations
Fairfield Inn & Suites
The Fairfield Inn & Suites Keene Downtown, located within a historic one-hundred-year-old building in the heart of downtown Keene, New Hampshire, invites you to relax in unique, boutique-like guest rooms. The Fairfield Inn & Suites Keene Downtown is a treasured gem overlooking Main Street and sits amongst area dining, shopping and artisans just footsteps from the hotel. Each of the uniquely styled guest rooms encompass the beauty and history of the century-old building while offering modern amenities such as free Wi-Fi, spacious work desks, crisp linens, pillow top mattresses and refrigerators. The Fairfield Inn & Suites Keene Downtown offers superior accommodations while providing the courteous service you deserve.
Hancock & Harrisville
Meals Provided
BreakfastAverage Mileage
28/55 milesElevation Gain
1,946/2,500 ftRiding Terrain
Rolling and hilly. Some gravel. Big climbs on the extra loopMeals Provided
BreakfastAccommodations
Fairfield Inn & Suites
The Fairfield Inn & Suites Keene Downtown, located within a historic one-hundred-year-old building in the heart of downtown Keene, New Hampshire, invites you to relax in unique, boutique-like guest rooms. The Fairfield Inn & Suites Keene Downtown is a treasured gem overlooking Main Street and sits amongst area dining, shopping and artisans just footsteps from the hotel. Each of the uniquely styled guest rooms encompass the beauty and history of the century-old building while offering modern amenities such as free Wi-Fi, spacious work desks, crisp linens, pillow top mattresses and refrigerators. The Fairfield Inn & Suites Keene Downtown offers superior accommodations while providing the courteous service you deserve.
Poocham Vineyard & Connecticut River Valley Ride.
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
35.8/55 milesElevation Gain
2,726/ 3,750 ftRiding Terrain
Rolling and hilly. Some gravel. Big climbs and gravel on the extra loopMeals Provided
Breakfast, Lunch, DinnerAccommodations
Fairfield Inn & Suites
The Fairfield Inn & Suites Keene Downtown, located within a historic one-hundred-year-old building in the heart of downtown Keene, New Hampshire, invites you to relax in unique, boutique-like guest rooms. The Fairfield Inn & Suites Keene Downtown is a treasured gem overlooking Main Street and sits amongst area dining, shopping and artisans just footsteps from the hotel. Each of the uniquely styled guest rooms encompass the beauty and history of the century-old building while offering modern amenities such as free Wi-Fi, spacious work desks, crisp linens, pillow top mattresses and refrigerators. The Fairfield Inn & Suites Keene Downtown offers superior accommodations while providing the courteous service you deserve.