Spring on Cheshire County NH roads and trails

May 9, 2022February 25, 2026 / Ellen Kolb

Cheshire County, New Hampshire is best known to outdoors enthusiasts for its most dramatic geological feature, Mount Monadnock. I have nothing against the mountain, except that I can’t seem to get to the summit and back without an injury of one sort or another. That’s not a problem. The Monadnock region offers plenty of options that have nothing to do with hiking uphill.

Rockwood Pond in Fitzwilliam , New Hampshire, with Mount Monadnock in the background. — _{Seen from the Cheshire Rail Trail in Fitzwilliam: Rockwood Pond with Mount Monadnock nearby. Photos by Ellen Kolb.}

As part of the New Hampshire Rail Trails Challenge, I’ve been exploring rail trails all over the state – but I’ve barely touched southwestern New Hampshire, aside from a few miles in the town of Troy. This is the year I’ll get busy out in that direction. I got off to a modest start recently on a short segment of the Cheshire Rail Trail in Fitzwilliam.

What a day! Weather was pleasant. The flying insects were not yet out in force (but alas, the same couldn’t be said for ticks; I came prepared with permethrin-treated clothing). Deciduous trees hadn’t yet leafed out. That left the hemlocks and pines to shade me, and as a bonus, the breeze through their boughs was like music.

Parking along long trails like the Cheshire can be a problem. Not every road crossing has room nearby for cars to pull over. I decided to begin my walk at Rhododendron State Park, a mile away from the trail. No trouble parking there. The park’s signature rhododendrons won’t be in bloom until July, but spring wildflowers abounded in the park’s grove and along its trails.

_{Spring flowers at Rhododendron State Park}

From there – pull out your maps app now – it’s a mile along unpaved Rockwood Road to the the intersection with rail trail along Rockwood Pond. Rhododendron Road provides a shorter but less interesting link.

The scenic highlight of the day was the view of Monadnock seen from the shores of Rockwood Pond. Pine trees tried to obscure the view, but I found my way through them.

From the pond, I headed south. The trail was unpaved, wide, and shaded. It’s a snowmobile trail when there’s snow cover, but motorized vehicles are supposed to stay off the rest of the year. Wide ruts in some soft sections of the trail told me that an ATV driver or two had ignored the restriction. Aside from that, the trail was in good condition between the pond and state road 119. South of there, the trail was full of roots and rocks, looking like a typical New Hampshire woods walk. I got as far as Royalston Road before turning around.

Monadnock Region summer sampler

July 22, 2018February 25, 2026 / Ellen Kolb

A summer Saturday, great weather, and no schedule to keep: this is as good as July gets.

pale pink rhododendron blossom — _{The blossoms that give Rhododendron State Park its name.}

I’ve never managed to get to Rhododendron State Park in Fitzwilliam, New Hampshire during peak bloom time, which is supposed to be mid-July, give-or-take. Even so, I’ve never had a disappointing trip there. The rhododendron grove is shady and cool, with or without blooms.

I skipped the trail leading from the grove to Little Monadnock Mountain. Instead, after a walk around the grove, I left the park via Rockwood Road to connect with the Cheshire Rail Trail at Rockwood Pond a little over a mile away.

Rockwood Road is unpaved but well-maintained, at least in midsummer. I walked the first half-mile with only a barred owl and a few tiger swallowtail butterflies for company. As I approached the pond, I passed a few houses and was passed by a few very polite drivers.

Last time I saw Rockwood Pond was on a foggy autumn weekday without another soul in sight. This time, there were picnickers at the shore and canoeists on the water. Not much traffic on the rail trail, though. In fact, the only other pedestrians I saw were in the grove at the park. Grove, road, and trail together made a great walking route for me. Bug repellent was useful.

pond with forest in the background and a dirt trail in the foreground — _{Rockwood Pond, Fitzwilliam, NH}

A map of the area suggests to me a longer loop hike for some other day: from the trailhead in Rhododendron State Park, go uphill to Little Monadnock; follow the Metacomet-Monadnock trail northward into Troy; turn south on the Cheshire Rail Trail; then turn right (south-southwest) on Rockwood Road to return to the park.

But no long hike for me today. Instead, after my walk I drove to discover a couple of places that were new to me (even though they’re apparently very well known by the rest of the world).

At Monadnock Berries in Troy, I picked about three pounds of scrumptious blueberries while enjoying a prime view of Mount Monadnock.
The Kimball Farm ice cream stand in Jaffrey was crowded, and I could have done without the smell of fried seafood being served a few windows over. But those are just quibbles. My ice cream cone, allegedly a “mini” portion (but don’t you believe it), was perfect.

blueberry farm with mountain in the distance — _{Monadnock and blueberries: a great combination. Photos by Ellen Kolb.}

Southwest NH: Cheshire County drive

December 11, 2015February 24, 2026 / Ellen Kolb / 4 Comments

I spent a foggy and snowless December day driving from the Merrimack River to the Connecticut River and back through New Hampshire’s southern tier, stopping for walks now and then. Visibility was too limited to make a mountain hike worthwhile, but rail trails and roadside parks were ready for me.

I chose a short segment between the nicely-restored depot in Troy and Rockwood Pond in Fitzwilliam. It was a round trip of just over four miles on a wide, straight trail. The only sounds were from birds and my own steps. No ice or snow, just a bit of mud on the southern half of the walk. On a clear day there’s a splendid view of Mount Monadnock from the shore of Rockwood Pond, though the fog obscured all the surrounding hills today.

DSCF0315 — _{Cheshire Rail Trail, Troy NH. All photos by Ellen Kolb}

Swanzey was next, and I managed to work a pair of the town’s famed covered bridges into my route. The most exciting sight of the day was a bald eagle I spotted near the Ashuelot River, and it was too swift for me to snag a photo.

DSCF0337 — _{Thompson Bridge in Swanzey, complete with sidewalk.}

The village of Ashuelot is in Winchester, with a covered bridge of its own.

DSCF0344 — _{Bridge in the village of Ashuelot, Winchester NH}

After some business in Brattleboro, Vermont, I took the more-or-less direct route back east, along New Hampshire routes 9 and 101. I stopped for a half hour at Chesterfield Gorge, a small roadside state park on NH route 9.

DSCF0363 — _{Enjoy Chesterfield Gorge with a three-quarter-mile loop walk from the parking area.}

DSCF0360 — _{Wilde Brook, which cuts Chesterfield Gorge.}

As the photos show, this is a very mild late autumn. In a fit of irrational exuberance, I almost tossed sandals in the car before I left home. Good thing I refrained; there was just enough mud and chill to make me glad I wore sensible shoes.