Epic Southern New Hampshire (and a Taste of Vermont)

The Charm and Beauty of Europe Close to Home

Experience five days of extraordinary rides offering the most challenging climbs and thrilling descents in New England

Destination

New Hampshire

Activity

Biking

Level

Advanced

Duration

5 days / 4 nights

Mile hungry cyclists who live in the Northeast and want a challenging five day cycling escape close to home.

From $2,395 PP 5 days / 4 nights

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Mile hungry cyclists who live in the Northeast and want a challenging five day cycling escape close to home.

The Charm and intensity of Europe cycling 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. This special edition of our classic New Hampshire tour offers harder rides and longer days in the saddle. It’s perfect for those who love to spin for hours while enjoying fascinating history, tiny villages, covered bridges, abundant lakes, cool forests, zigzagging rivers, farmland, and magic moments galore!

Discover the rich history, pristine landscapes, and gorgeous backroads of the Monadnock Region. 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 intermediate and advanced riders.

The intense-in-every-way cycling loops in Keene include a dive into the colonial and Native American past of North America. You’ll experience mile after mile of gorgeous scenery and a glimpse into the connective tissue of our nation’s past. Spin over miles of 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.

Keene is the perfect cycling hub for interesting and savory post ride wandering; it is 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. The entire downtown is framed by one of the most beautiful Main Streets in the world with the picturesque United Church of Christ at the top of Keene’s Central Square.

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
Ascents of many legendary climbs (including Mount Ascutney and Lemptser Mountain)
Pedal over and through the region’s abundant covered bridges and stone bridges
Visits to art galleries and craft shops
Honey and Liquor 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
Optional 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
Explore our Top Photos from our Southern New Hampshire Bike Tours

What to Expect

Terrain

Rolling and hilly

Start Location

Keene, New Hampshire

End Location

Keene, New Hampshire

Mileage

Average Daily: 57 Total: 286

Elevation

Average Daily: 4,300 feet Total: 22,000 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.

Bring your own bike! Bikes are not included for this specific trip.

Call us if you need a rental bike!

All accommodations (4 nights at Fairfield Inn and Suites)
All breakfasts, 3 lunches, 3 dinners
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, 3 lunches, 3 dinners

Itinerary

Start Location

Keene, New Hampshire

Fly Into

Manchester, NH

End Location

Keene, New Hampshire

Fly Out Of

Manchester, NH

Download Itinerary

STYLED MAP

Day1

Swanzey

We’ll meet the group at 12:00 pm at the Fairfield Inn & Suites for introductions. Come prepared for riding as we’ll head out for our first ride after a quick safety overview. The ride will begin on the flat roads alongside Wilson Pond and allow everyone to begin disconnecting from the stress and pressure of everyday life. We won’t hit any significant climbs today—the only bump on the agenda will be a picturesque rural climb alongside a former fish hatchery. For those riders looking to stretch their legs for the coming days, the return trip includes a wonderful flat road section for a challenging stretch. Upon our return to Keene, we’ll have a walking tour of downtown and the Walldog Murals that tell the story of Keene's most important places and personalities.

Average Mileage

39 miles

Elevation Gain

1724 ft

Riding Terrain

Flat and rolling

Accommodations

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.

Luxury Level3 star

Day2

Can You Tame Leviathan?

We start day 2 with a perfect warmup on the dirt surface of the flat Ashuelot Rail Trail before taking the tour to roads where you can assess or work on your ability to ride and operate as a group on a three-mile flat road section perfect for tempo pace. We follow that with a one-mile climb at 8% grade and a quick stop for a snack before entering Massachusetts and hitting another five-mile segment with small rollers. All of this sets the stage for a climb of a legendary four-mile climb at 4% grade that is featured in the Harpoon Brewery’s B2VT Ride. If you’re looking for advice on how to attack the climb, you can turn to Ciclismo Classico guide Mark Miller as he has the second-fastest time among the more than 2000 riders who’ve tackled this segment on Strava. We’ll stop for a picnic lunch in downtown Chesterfield before returning to Keene via scenic roads alongside Lake Spofford. All of this is punctuated with a fantastic recovery meal at Luca’s Mediterranean Café in downtown Keene.

Meals Provided

Breakfast, Lunch, Dinner

Average Mileage

49 miles

Elevation Gain

3,123 feet

Riding Terrain

Rolling and hilly with two big climbs

Meals Provided

Breakfast, Lunch, Dinner

Accommodations

Fairfield Inn & Suites

Luxury Level3 star

Day3

The Challenge of Ascutney

Today we will take on one of the hardest climbs in the country: Mount Ascutney. At 3.6 miles, many climbs are longer than the famed Vermont mountain. However, Ascutney is not known for its length—it’s known for its steepness. At 12% average grade, the climb ascends over 2200 feet in its relatively short length. With grades steeper than Mount Washington, Ascutney’s fastest ascents have all measured under 10MPH average speed. Ascutney isn’t the only climb on the agenda, however. Riders will have the chance to warm up on a 1.5-mile, 8% average grade earlier in the ride. After the hard climbs, riders will have a chance to enjoy flat-to-gently rolling roads through New Hampshire farm country. We’ll finish our day with a visit to Burdicks Chocolate Factory in Walpole, NH before we refuel for the evening at Machina Kitchen & ArtBar. For those interested, we can finish our day at the local speakeasy—be prepared though…you’ll need to crack a riddle to gain admittance before New Hampshire Magazine’s 2020’s top bartender will mix you up an award-winning drink.

Meals Provided

Breakfast, Lunch, Dinner

Average Mileage

62 miles

Elevation Gain

6,010 ft

Riding Terrain

Big climbs through the rural countryside

Meals Provided

Breakfast, Lunch, Dinner

Accommodations

Fairfield Inn & Suites

Luxury Level3 star

Day4

Lempster Mountain Shakedown

Our Queen stage starts innocently with 10 miles of gently uphill roads and the scenic ride over Surry Mountain Dam as we warm-up before starting the day’s climbs. The first climb clocks in at 1 mile and 7.5% average grade—it will feel even more difficult after the previous day’s efforts on Ascutney. From there we will traverse flat-to-gently rolling roads before we begin an ascent of Lempster Mountain. Picturesque wind turbines provide a scenic backdrop as you climb 1.1 miles at 9% average grade. We’ll regroup for lunch on the village green in Washington before we begin the long return. Along the way we’ll test the legs two more times—once on a short .7 mile climb at 8% average grade and a final time on a nearly 3-mile climb that features grades averaging over 5%. The return journey includes several long, flat sections of road (one measuring 7 miles and the other 5) as a reward for the day’s earlier efforts.

Meals Provided

Breakfast, Dinner

Average Mileage

87 miles

Elevation Gain

6,729 ft

Riding Terrain

Rolling and hilly with two main climbs

Meals Provided

Breakfast, Dinner

Accommodations

Fairfield Inn & Suites

Luxury Level3 star

Day5

Cycling Around Monadnock

Just because it’s the final day doesn’t mean things are going to be easy. The .9 mile climb at 9% grade five miles into the ride sets the stage for repeated punchy hills that will evoke memories of the Ardennes classics. It won’t all be suffering, however, as we’ll visit the village of Nelson and stop by Slovenia Beekeeping for a quick honey and liquor tasting and step back into time at the Harrisville General Store. Built in the 1800s by Cyris Harris during the heyday of Greek Revival architecture, the store retains elements of that style and evokes images of a Greek temple. From there we’ll circle and see stunning views of Mount Monadnock. We’ll finish the ride with an ascent to the scenic vista from atop Otter Brook Dam before we tackle a final one-mile climb averaging 5% grade. There’s also an option to skip the last 20 miles of riding and ascend Mount Monadnock…a 2.1-mile hike that ascends more than 1600 feet to panoramic views atop the mountain.

Meals Provided

Breakfast

Average Mileage

48.6

Elevation Gain

4,116

Meals Provided

Breakfast

Accommodations

Epic Southern New Hampshire (and a Taste of Vermont)

Luxury Level

Meet Our Guides

Lauren Hefferon

Guide Since 1988

From the Blog

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Italy

2023 Tours

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By Ability Level

Epic Southern New Hampshire (and a Taste of Vermont)

The Charm and Beauty of Europe Close to Home

Destination

Activity

Level

Duration

Tour Essence

What to Expect

Terrain

Start Location

End Location

Mileage

Elevation

What's Included

Itinerary

Start Location

Fly Into

End Location

Fly Out Of

Swanzey

Average Mileage

Elevation Gain

Riding Terrain

Accommodations

Fairfield Inn & Suites

Can You Tame Leviathan?

Meals Provided

Average Mileage

Elevation Gain

Riding Terrain

Meals Provided

Accommodations

Fairfield Inn & Suites

The Challenge of Ascutney

Meals Provided

Average Mileage

Elevation Gain

Riding Terrain

Meals Provided

Accommodations

Fairfield Inn & Suites

Lempster Mountain Shakedown

Meals Provided

Average Mileage

Elevation Gain

Riding Terrain

Meals Provided

Accommodations

Fairfield Inn & Suites

Cycling Around Monadnock

Meals Provided

Average Mileage

Elevation Gain

Meals Provided

Accommodations

Epic Southern New Hampshire (and a Taste of Vermont)

Meet Our Guides

Lauren Hefferon

From the Blog

The Best Bike Rides in Southern New Hampshire

Cycling through Southern New Hampshire – A Taste of Tuscany Close to Home!

Top Photos from Southern New Hampshire

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