Hitting the Road in Tolland County

The small towns of Connecticut’s smallest county are best explored through a good old-fashioned drive in the country.

The back roads of Tolland County traverse rural landscapes and towns that haven’t changed much since the 18th century. They also find their way past modern communities and people going about their lives, unaware, perhaps, that where they live is perfect for road-tripping. I wanted to see what I’d stumble across in this relatively little-traveled part of the state.

I started at the impressive Eagleville Dam, where water flows flat as a tabletop before cascading downwards. I drove into Mansfield, past the old Town Hall building, now a , the historic , and the  with its bright red doors. Little girls in skirts twirled on the lawn.

I drove north to Willington, where I found the town common at Common Road (naturally) and Jared Sparks Road, named after the historian and Harvard President who is Willington’s best-known native. The only movement amidst the churches and old houses came from a man mowing a lawn. Past the Old West Cemetery, on a small hill, I continued north beside the Willimantic River, which appeared occasionally, a black ribbon flowing beside the road.

A “Congested Area” sign warned that Stafford Springs, where Main Street wraps itself around a fountain and climbs a hill lined with storefronts, would be bustling. I stopped at the Middle Ground Café, in a brick building by the train tracks, near where an arched stone bridge crosses the Middle River. The area’s namesake springs were once renowned for their healing properties by local Indians and settlers alike. I found one - a source of “iron water” - beside the Stafford Historical Society’s Museum on Hyde Park.

I continued west to Somers, which was part of Massachusetts until 1749. I knew nothing of this rural town except two bits of trivia: it once had a bonnet-making industry, and Stonewall Jackson’s favorite horse was born here. Flowers bloomed everywhere. On the common, I found a whimsical blue-grey 1896 library building, now a .

In Ellington, where neat historic houses lined up in rows near an elongated common, it seemed like the entire population had turned out for the weekly  in . In Crystal Lake, a Census Designated Place within the town, I stopped at . The area had a distinct personality, as if focused more on swimming than farming.

In quiet Tolland, I found a narrow town green and eclectic buildings of various styles. The most remarkable of these was the old . It’s not the first jail to be built here, and over the years it’s been both augmented and downsized; an attached hotel burned down in 1893. But it’s certainly one of the most improbable jail buildings I’ve seen.

Bolton, with pristine white buildings and a green not much larger than a yard, was even quieter. A colorful waving flag led me to the Fish Family Farm, where up a long driveway past cows lolling in the grass I found a white barn and ice cream. Just past the center of town I found Heritage Farm. This property, where Rochambeau’s army camped in 1781, was purchased by the town in 2000 to prevent development. Its house and farm buildings, and softly rolling land with extensive stone walls, seemed the perfect place to end my drive.

Many roadside sights tempted me along the way, but there wasn’t time in the day for all of them. I’m sure that if I came back this way again, I could find all sorts of other places, and that anyone who tried a different route through the same place would find still more.

If you go:

Eagleville Dam and Lake

Route 275, Mansfield


Middle Ground Café

42 Main Street, Stafford


Mon – Wed, 6am – 3pm, Thu – Sat, 6am – 8pm, Sun 7am – 3pm


Hyde Park, Riverside Section

Off of Spring Street, Stafford

There is parking behind and across from the Stafford Historical Society Museum.


Ellington Farmers Market

Arbor Park, Main Street, Ellington

Sat, 9am - Noon


Sandy Beach

Sandy Beach Road, Ellington

The beach is open to non-residents. For information on season dates, hours, and fees, click here.

Bolton Heritage Farm

Bolton Center Road, Bolton

There is limited parking by the house and farm buildings.

For more information about the Rose Trail, click here.

Fish Family Farm

20 Dimock Lane, Bolton


Mon – Sat, 11am – 8pm



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