La Piazza Blog & Stories
The Best Bike Rides in Southern New Hampshire
August 25, 2020

The Best Bike Rides in Southern New Hampshire

All Based out of Picture Perfect Bike Hub Keene, NH!

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.” Join me in discovering the rich history, pristine landscapes and gorgeous backroads that inspired my passion for bicycle travel.

I selected my favorite cycling loops from Keene that include historic architecture, art galleries, covered bridges, abundant lakes, cool forests, zigzagging rivers, farmland galore and daily views of the region’s crowned granite jewel, Mt Monadnock, (Mountain That Stands Alone) the second most climbed mountain in the world.   Ride these on your own or join us on tour! (Private tours available too.)

Ride #1: Surry, Walpole, Alstead and Gilsum (51 Miles)

Southern NH: Gold mines, Wineries, world-famous chocolate  & more…who knew?

One of my favorite villages and Southern NH rides is to the town of Walpole incorporated in 1756 and named in honor of Sir Robert Walpole, the first prime minister of Great Britain.

Walpole is one of New England’s prettiest villages. Many of its beautiful and historic buildings have been restored by its residents, so today’s town looks much as it did years ago. 

Along the way you can stop in the tiny village of Surry, chartered by Charles Howard, Earl of Surrey, framed by the massive 4-mile wall of Surry mountain, once mined for mica, copper, silver, and gold and now 1,368 acres of a future nature preserve that is home to bears, bobcats and migratory birds.  

From Surry climb a blend of silky & gravel roads to Barnett Hill and the Walpole Mountain View Winery. The descent to Walpole is a screaming, five star epic 3 miles to pristine Walpole, home to artists, writer Dayton  Duncan, filmmaker Ken Burns and Larry Burdick, the founder of Burdick Chocolates, who after being inspired by the chocolate makers of Bern, Switzerland, set up shop in Walpole in the late ’70s with his wife Paula where they began creating their unique and world-famous chocolate Burdick mouse and other stylish chocolates. The Burdicks have a restaurant and chocolate shop next to the general store and tiny post office.

From Walpole, it’s onto Drewsville founded by Thomas Collins Drew who bought the land that would become the village of Drewsville in 1810. The power of the Cold River and Blanchard Brook resulted in the now sleepy Drewsville to become a center of manufacturing through the mid 1800s. By the late 1800s, the arrival of rail lines and the transporting of northern timber with massive log drives on the Connecticut River resulted in remarkable growth in North Walpole.

Up, up, up to Alstead and East Alstead, that despite its small size, is a village rich in colonial history. It was chartered by Governor Jonathan Belcher as one of the nine forts established to protect NH from attack by the Native Abenaki.  Named after Heinrich Alstead who compiled an early encyclopedia,  the town also wavered its allegiance to NH and decided to join Vermont until George Washington had a thing or two to say about it and Alstead changed its mind. Alstead, formally known as “Paper Mill Village”, was the location of the State’s First Paper Mill. Paper was then a rare and expensive product (Go figure!). While Alstead was mostly an agricultural community, its streams and ponds powered many small mills.

At the very top of the climb is the lovely Lake Warren, pedal along its quiet shores then a super long steep downhill to Gilsum situated along the Ashuelot River and home to The Stone Arch Bridge completed in 1863 and has the highest vault of any mortarless bridge in NH. 

Climb up to Gilsum road then a breathtaking easy ride along the Ashuelot which provided power for the abundant woolen mills in the area. It is hands down, one of my absolute favorite rides ever! 

Take back roads to Surry Mountain Dam – built to help control the floodwaters of the Connecticut River. For years many towns and farms along the river had sustained significant damage due to flooding, and in the early part of the 20th century, it became evident that something needed to be done. The construction was carried out by the Army Corps of Engineers, and the dam in Surry was the first to be built. It was an ideal location because it was close to the city of Keene and there would be minimal displacement of people in the town of Surry. Riding the straightaway along the dam, with Surry mountain to the right, the lake below it is a sight to see! Glide back to Keene along East Surry Road, past the glowing green Brentwood Golf Course, past Goose Pond and down Court Street with its lovely period homes.

RIDE #2: Westmorland. Lake Spofford. Chesterfield. (55 Miles)

This ride begins on Hurricane Road, a few blocks from my childhood home. It was named after the Hurricane of 1938, one of the most devastating in US history. Poor Keene certainly took a beating but it bounced back as it always has. Passing through open farmland and dense forest, it’s a lovely descent to Westmorland, another fort town established to protect the colonies from attack from the Abenaki who enjoyed their camps along the nearby Connecticut River (who wouldn’t). A rolling ride along River Road that parallels the Connecticut River and then left up, up and up on Poocham Road, named after the nearby Poocham, an unincorporated community. Poocham comes from the Abenaki word meaning a gathering place. The steep climb toward Spofford Lake passes The Poocham Vineyard (who knew?) and several private family graveyard plots including The Roberston Family, descendants of my childhood friend, Joji Robertson.

Now a taste of a juicy modern murder mystery in the middle of nowhere. On my descent to Spofford, you’ll note a mansion and vast property that belongs more in France than Southern, NH.  I discovered thanks to Joji that it is the home of real estate mogul John Chakolas who was murdered in 2013, apparently by his grandson, Nathan Carman, who has been also accused of pushing his mother overboard while on a fishing trip. 

The gravel portion of this ride goes to Madame Sheri Forest and the Madame Sherri’s Castle Ruins, a place of legends and lavish parties. The medieval-looking ruins continue to spark the imagination. Gatsby may have been a figment of F. Scott Fitzgerald’s imagination, but New England has its very own, very real version of the larger-than-life character: its local queen of scandal, Madame Sherri. The glamorous eccentric threw fabulous parties at her “castle” in the middle of the forest, and drove around the town in a custom-made cream Packard car, with a monkey perched on her shoulder.

The final miles pass beautiful Spofford Lake where you can enjoy a dip in one of the cleanest lakes in Southern, NH and interestingly where actor-comedian George Carlin spent his summers as a child and part of his ashes are scattered in the lake. Over to the village of Chesterfield Center with its beautiful granite stone buildings.

This town was the site of Fort number one, the first in the line of forts bordering the Connecticut River. The town named after Philip Stanhope, 4th Earl of Chesterfield but its first settlers were Moses Smith and William Thomas who, with their families, came up the Connecticut River in canoes in the fall of 1761. That winter they lived on the abundant salmon and shad of the river that divides Vermont and NH. Live Free or Die it is.

Before our final roller gravel ride back to Keene, we stop at the Chesterfield Gorge, a geological wonder that just happens to have a series of horsetails, cascades, slides, and plunges in its midst.  A few more climbs along Atherton Road past the Town Pound (where stray animals and tax evaders were taken) and Pisgah State Park, the largest State Park in NH.

Final descent, finally down Chesterfield Road and back on the bike path to Stonewall Farm and along the Cheshire Rail Trail all the way back to Keene.

RIDE #3: Sullivan- Nelson- Hancock- Harrisville. 60 Miles

This ride spins through tiny pristine rural villages established in the 1700s that were once bustling mill towns and are now they are magical havens of artists, poets, and musicians. 

One historian writes:

“There were those who settled here with skills of carpentry, brick making and laying stone, and those who could sing and dance and write poetry. There were men who went to war, and some never came back. There were those who raised sheep, and those who made mills and ran them, and those who taught school, and some of the men served in the State Legislature. Everyone farmed, at least for a while. And lots of people told stories and some of them wrote them down, and some of them are true.”

Along the way we pass the Harris Center, a conservation center and super sanctuary of 35,000 acres of preserved land and historic

My all-time favorite village is Harrisville; it’s red-bricked buildings and stunning mills are surrounded by small ponds & lakes: Child’s Bog, Nubanusit, Chesham Pond, Skatutakee and Silver Lake, the picture-perfect swimming hole of my youth. All frozen in time!

Harrisville is a unique mill village that preserves the scale and setting of the numerous mill villages that were built on waterpower sites throughout New England prior to the Civil War, during the early stages of America’s Industrial Revolution. Today the village retains its two early textile mills together with a range of related buildings – boarding houses, workers’ cottages, owners’ houses, a store, meeting house, school, dams, and mill ponds. The general store has preserved the charm and penny candy of yesteryear.

On our return and just outside of Keene is the Stone Arch Bridge is a stone arch railroad bridge in Keene, Cheshire County, New Hampshire, United States. Built in 1847 to carry the Cheshire Railroad, it is one of the best-preserved pre-1850 stone arch bridges in the nation. The bridge was listed on the National Register of Historic Places in 2012. We finish the ride in Keene– be sure to take a walk around town and check out the Walldog Murals a fascinating community project that depicts the history of Keene and the Monadnock Region. Walk around and visit all 17 murals, you will feel uplifted, feel hopeful about community and what people can do when they work together to recreate history.  “To see a dream become the seed of an idea and then a reality, accumulating friends and fellow dreamers along the way who shared the vision…is simply as good as life gets” P. Poanessa

Put Keene, NH on your must-visit places (to bike)!

Ride these on your own or join us on our bike tour! (Private tours available too.)


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