The town of Tolland got its name in 1715 and is the seat for Tolland County, which takes up a big chunk of northeastern Connecticut.
In the past Tolland was vested with administrative and judicial roles, signs of which are still here on the picturesque Town Green.
Tolland has an active historical society, opening centuries-old properties to the public in summer, including the old courthouse and jail on the green.
Natural space is all around Tolland, and you can haul yourself through the treetops at The Adventure Park at Storrs or ascend Soapstone Mountain in Somers for vistas spanning the Connecticut River Valley.
1. Tolland Green Historic District
Centered on Tolland’s long and narrow Town Green is a historic district with over 50 contributing buildings, most of which are fine residences from the 18th and 19th centuries.
The green has had the same basic footprint for almost three centuries, and in its earliest years the south end was the site of the first congregational church, in a log building.
Facing off now on the southern tip are the Old Town Hall (1879) and the current Town Hall (1909). As the county seat, Tolland was bestowed with a county courthouse and jail, both of which are looked after by the Tolland Historical Society and can be entered in summer (more later). With the absence of fencing and curbs, the green looks much as it did 200 years ago, save for asphalt on the roads.
Drop by the Tolland Red & White at No. 46, a lovable little shop selling penny candy and antiques.
2. Daniel Benton Homestead Museum
The Tolland Historical Society operates three museums in the town, the first of which is out in the countryside to the south.
This is the Daniel Benton Homestead, where six generations of the Benton family lived, from the first half of the 18th century to 1932. The sons of its founder, Daniel Benton, fought in the French and Indian War, and five of their sons were spurred to action by the Lexington Alarm Letter (1775) and fought in the Revolutionary War.
Daniel Benton would still recognize his homestead today, right down to the light Prussian blue wood-paneling in the parlours.
There’s an original walk-in fireplace with rear-bake oven in the kitchen, while the cellar was used to hold British and Hessian prisoners during the Revolutionary War.
Visit on Sunday afternoons, June through September.
3. Old Tolland County Jail and Museum
As we’ll see, in the 19th century Tolland was the judicial center for the whole county.
Anybody awaiting trial accused of felony crimes, or given a custodial sentence of up to a year would do their time at this jail, built in 1856 (the fourth on the site). The jail functioned from this time to 1968, and the rather decorative jailer’s home in front was raised in 1893. The Tolland Historical Society will show you around on Sunday afternoons, 13:00-16:00, June through September, although you can book appointments at other times.
The 32 cells have been preserved as they were when the jail closed, and you’ll hear stories about former inmates, and of the County House, a hotel that was attached to the jail providing lodging for people who had business with the courts.
4. Tolland County Courthouse Museum
It’s worth combining a visit to the Old Tolland County Jail with the historic courthouse opposite, also in the hands of the Tolland Historical Society.
This solemn building was constructed in 1822 (replacing one from 1775) and was the site of all court sessions in Tolland County for the next 70 years.
From the green the most striking part of the building’s outline is the belfry, crowned with a round cupola.
The courtroom, restored to its 19th-century appearance, is on the second floor where there’s a fine Palladian window and cove ceiling.
At the back are information panels explaining the history of the building and the impact of the county courthouse and jail on the development of Tolland in the18th and 19th centuries.
5. The Adventure Park at Storrs
In the woods to the south-east of Tolland there’s a high ropes course with eight different trails.
You’ll make your way between tree-top platform via more than 80 different transitions, made from rope, wood or cable.
All of the courses have at least two zip-lines, while the Pine Rush trail has six, including the park’s highest and longest.
If all this sounds scary, you’ll be provided with a harness and all safety equipment, and will be given a safety briefing to show you how to tackle all these bridges and zip-lines.
6. Crandall Park
A treasured local amenity, Tolland’s 300-acre town park accommodates multiple outdoor activities.
First off, there are five miles of wooded trails, and Crandall Pond has a beach open for swimming during the school summer break.
Fees apply, but these are affordable even for non-residents.
As well as swimming lanes, the beach has a diving board and raft.
Elsewhere, there are tennis courts, a children’s play area, three baseball/softball fields and a mixed-use field for soccer and other sports.
For special occasions the town also rents out a pavilion and a lodge in the park.
7. Birch Mountain Pottery
At 223 Merrow Road in Tolland you’ll come to the store and studio for ceramicist Susan Gerr, who has been working in clay for three decades.
She makes handcrafted functional pottery (casseroles, mugs, sushi sets), all playing with contrasting elements like smooth or textured surfaces, or glazed or unglazed areas.
If you’re in the area you can put your name down for evening classes with Susan, taking place across eight weeks and starting in September, January and April.
These cater to beginner, intermediate and advanced potters, teaching techniques and methods like hand-building, wheel-throwing and decorating.
8. New England Motorcycle Museum
At the cavernous, 200-year-old Hockanum Mill in neighbouring Vernon, the motorcycle enthusiast Ken Kaplan has opened a museum with scores of bikes from more than 25 brands.
These are set out on two floors, one dedicated to Harley Davidson and vintage brands like Indian, and another for off-road bikes by the likes of Honda and Kawasaki.
These gleaming machines are all presented along with a massive library of magazines and memorabilia relating to some of motorsport’s biggest events and personalities.
When we wrote this article in September 2019 a motorcycle-themed bar, restaurant and microbrewery was in the works on the first floor.
9. Cassidy Hill Vineyard
You could escape for a while to the Connecticut hills, tasting reds, whites and rosés at Cassidy Hill’s welcoming winery.
This is set in a rustic pinewood log cabin, and every Friday night in summer there will be live music on the porch.
A tasting session with five wines will cost $7 and for $10 you’ll get a Cassidy Hill logo class to take home.
The rosé, Pink Catawba, made from America’s oldest native grape variety, won “Best in Show” at the Connecticut Wine Society’s 2018 Amenti del Vino.
10. Shenipsit State Forest
Beyond the west side of Tolland you can get onto the Blue-Blazed Shenipsit Trail, which goes south, along the eastern lip of the Connecticut River Valley for 50 miles to the Meshomasic State Forest.
The highest point on the trail is local, at Soapstone Mountain within the Shenipsit State forest.
At the summit you can climb a new observation tower, raised in 2018, for a view that extends across the Connecticut Valley and up to the skyline of Springfield in Massachusetts.
The Shenipsit State Forest is 11 parcels of land in Somers, Ellington and Stafford, adding up to almost 7,000 acres and growing mostly red oak.
At the forest’s HQ in Stafford is the last survivor of the 21 Civilian Conservation Corps (CCC) barracks in Connecticut, preserved here as a museum about this Depression-era organization.
11. Fox Hill Tower
You could make the five-mile drive west to Rockville for a marvellous view of the Connecticut River Valley at this historic site.
The first building at Fox Hill was a wooden observation tower raised in the 1870s but falling victim to a blizzard in 1880 and left to deteriorate over the next few decades.
A new octagonal stone structure was completed by Works Progress Administration in 1939 as an employment initiative during the Great Depression.
This 22-meter monument, together with its 67-meter promenade stands as a tribute to the veterans of all wars from the town of Vernon.
Close to the top is an observation platform where the Metacomet Ridge’s Talcott Mountain, Mount Holyoake and Mount Tom are all visible across the valley on a clear day.
12. Nye-Holman State Forest
You can stroll next to the Willimantic River at this 50-acre patch of riverside meadow and sloping woodland in Tolland.
In 1720 this land was granted to one Ebenezer Nye to establish a homestead and work a toll bridge on the river.
This parcel was handed down as a farm through six generations of the same family before Nye’s great, great, great granddaughter Alice Holman Hall gave it to the state in 1931. From the gravel forest road you can get down to an unmarked trail, meandering for half a mile on the riverbank, hemmed by ferns as well as wildflowers in spring and summer.
This length of the Willimantic is a trout management area, popular with anglers for catch-and-release fly-fishing.
13. Stafford Motor Speedway
Comes a time when you need some high speed action, and the answer to that craving is a few miles away at the short-track Stafford Motor Speedway.
Before the days of automobile racing this exact course was a racetrack for horses, laid down in 1870. Stafford Motor Speedway is an accredited NASCAR Whelen All-American track, and holds three Whelen modified tour events between May and September.
Outside the weekends when the tour is in town, there’s heart-pumping racing for a bill of modified stock car divisions every Friday night, and room for 8,000 spectators so you’ll always get a good seat.
14. John Cady House
If you’re driving through rural Tolland there’s a significant building at the corner of Mile Hill Road and Cedar Swamp Road.
This is the John Cady House (c. 1720), thought to have built by the elder John Cady, who came from Massachusetts, which would explain why this Georgian Colonial house resembles others from the neighboring state more than Connecticut.
On a wood frame this 2.5-story structure is five bays wide and has a portal traced by Greek Revival pilasters.
An interesting detail is that what is now Mile Hill Road was rerouted later in the 18th century from the west side of the property to the east, and in the late-1700s the John Cady House served as a tavern.
The house is a private property, but is worth looking out for as you pass by.
15. William Benton Museum of Art
The Storrs campus for the University of Connecticut is nearby and has a highly-regarded art museum named for the university’s former trustee and senator for Connecticut.
The Benton opened in 1967, in a building dating back to 1920 and initially serving as the university’s main dining hall.
The museum’s inventory has grown since then to more than 6,500 pieces.
The collection is most noteworthy for its American art, by Childe Hassam, Emil Carlson, Mary Cassatt, Edward Burne-Jones and Ellen Emmet Rand, but also has pieces by the likes of Gustav Klimt and Käthe Kollwitz.
In autumn 2019 there were engaging temporary shows for Reginald Marsh’s tropical watercolours, and African art acquired by former Professor Emeritus of Sociology Josef Gugler and his wife Janine Gugler.