Top 15 Attractions and Activities in Tolland, CT

The town of Tolland was established in 1715 and serves as the seat for Tolland County, which encompasses a substantial portion of northeastern Connecticut.

Historically, Tolland held administrative and judicial significance, with evident reminders observable in the scenic Town Green.

The town boasts an active historical society that opens historical properties to visitors during the summer, including the old courthouse and jail situated on the green.

Natural beauty surrounds Tolland, with opportunities for adventure such as traversing treetops at The Adventure Park at Storrs or climbing Soapstone Mountain in Somers for panoramic views of the Connecticut River Valley.

1. Tolland Green Historic District

The historic district encircling Tolland’s elongated Town Green features over 50 contributing structures, predominantly elegant residences from the 18th and 19th centuries.

This green has maintained its fundamental layout for nearly three centuries, with the southern end originally home to the first congregational church, constructed from logs.

At present, the southern edge showcases the Old Town Hall (1879) and the current Town Hall (1909). As the county seat, Tolland was equipped with a county courthouse and jail, both managed by the Tolland Historical Society, which opens these sites to the public during the summer (details provided later). Notably, without the presence of fencing or curbs, the green appears remarkably similar to its state two centuries prior, apart from the asphalt roads.

Make sure to stop by Tolland Red & White at No. 46, a charming shop featuring penny candy and antiques.

2. Daniel Benton Homestead Museum

The Tolland Historical Society manages three museums in the town, with the first located in the countryside to the south.

This museum is the Daniel Benton Homestead, where six generations of the Benton family resided from the first half of the 18th century until 1932. The progeny of its founder, Daniel Benton, participated in the French and Indian War, and five of his sons were motivated to serve by the Lexington Alarm Letter (1775), participating in the Revolutionary War.

Daniel Benton would still identify his homestead today by the light Prussian blue wood paneling in the parlors.

The kitchen hosts an original walk-in fireplace with a rear-baked oven, while the cellar historically accommodated British and Hessian prisoners during the Revolutionary War.

Visitation is available on Sunday afternoons from June through September.

3. Old Tolland County Jail and Museum

During the 19th century, Tolland served as the judicial hub for the entire county.

Individuals awaiting trial for felony charges or serving custodial sentences of up to one year would do their time in this jail, established in 1856 (the fourth on this site). The jail operated until 1968, with the notable decorative jailer’s residence in front built in 1893. Guided tours by the Tolland Historical Society occur on Sunday afternoons from 1:00 PM to 4:00 PM, June through September, with additional appointment availability at other times.

The original 32 cells have been preserved in their state upon closure, providing insight into the stories of former inmates and the County House, which functioned as a hotel attached to the jail, catering to those engaged with the courts.

4. Tolland County Courthouse Museum

Visiting the Old Tolland County Jail alongside the historic courthouse opposite is highly recommended, as both establishments are overseen by the Tolland Historical Society.

This solemn edifice was constructed in 1822 (replacing a structure from 1775) and served as the venue for court sessions in Tolland County for the subsequent 70 years.

From the green, the most prominent feature of the building is its belfry, topped with a round cupola.

The courtroom, which has been meticulously restored to retain its 19th-century appearance, is located on the second floor, showcasing a beautiful Palladian window and cove ceiling.

Informative panels at the rear explain the history of the building and the significant role of the county courthouse and jail in Tolland’s development during the 18th and 19th centuries.

5. The Adventure Park at Storrs

Located in the woods southeast of Tolland, there exists a high ropes course featuring eight distinct trails.

Participants navigate between treetop platforms using over 80 various transitions, constructed from rope, wood, or cable.

All courses include at least two zip lines, while the Pine Rush trail boasts six, encompassing the park’s highest and longest zip lines.

For those apprehensive of heights, safety equipment and harnesses are provided, along with a comprehensive safety briefing detailing how to navigate the bridges and zip lines.

6. Crandall Park

A cherished community resource, Tolland’s 300-acre town park supports a variety of outdoor pursuits.

Primarily, there are five miles of wooded trails, along with Crandall Pond, which opens for swimming during the school summer break.

While fees apply, they remain affordable even for non-residents.

The beach features designated swimming lanes, a diving board, and a floating raft.

Additionally, amenities include tennis courts, a children’s playground, three baseball/softball fields, and a versatile field suitable for soccer and other sports.

For special events, the town offers pavilion and lodge rentals within the park.

7. Birch Mountain Pottery

Located at 223 Merrow Road in Tolland, you will find the studio and store of ceramic artist Susan Gerr, who has been passionately working with clay for three decades.

She specializes in crafting functional pottery items such as casseroles, mugs, and sushi sets, each demonstrating various contrasting elements such as smooth versus textured surfaces and glazed versus unglazed areas.

For those interested in hands-on experience, evening classes with Susan are available, running eight weeks and commencing in September, January, and April.

These classes cater to individuals at beginner, intermediate, and advanced levels, covering techniques including hand-building, wheel-throwing, and decorative methods.

8. New England Motorcycle Museum

Located in the expansive Hockanum Mill, a 200-year-old structure in the neighboring Vernon, motorcycle enthusiast Ken Kaplan has curated a museum housing numerous motorcycles from over 25 renowned brands.

The exhibit spans two floors, one dedicated to Harley Davidson alongside vintage brands like Indian, while another floor showcases off-road motorcycles from manufacturers such as Honda and Kawasaki.

These brilliant vehicles are complemented by a vast library of magazines and memorabilia focused on significant events and personalities in motor racing.

As of September 2019, plans for a motorcycle-themed bar, restaurant, and microbrewery were underway on the first floor.

9. Cassidy Hill Vineyard

Consider a brief retreat to the Connecticut hills, where you can savor reds, whites, and rosés at Cassidy Hill Vineyard’s inviting winery.

The rustic pinewood log cabin houses this vineyard, which hosts live musical performances on the porch every Friday night during the summer.

A tasting experience, featuring five wines, is priced at $7, and for an additional $10, you can take home a Cassidy Hill logo glass.

Notably, the rosé, Pink Catawba, made from America’s oldest native grape variety, received the esteemed “Best in Show” award at the Connecticut Wine Society’s 2018 Amenti del Vino.

10. Shenipsit State Forest

On the west side of Tolland lies the Blue-Blazed Shenipsit Trail, which stretches southward, tracing the eastern ridge of the Connecticut River Valley for 50 miles towards the Meshomasic State Forest.

The highest elevation along this trail is found at Soapstone Mountain, within Shenipsit State Forest.

At the summit, a new observation tower constructed in 2018 offers visitors breathtaking views across the Connecticut Valley, extending to the skyline of Springfield, Massachusetts.

Spanning 11 parcels of land in Somers, Ellington, and Stafford, Shenipsit State Forest comprises nearly 7,000 acres dominated primarily by red oak trees.

The forest headquarters in Stafford houses the last remaining of the 21 Civilian Conservation Corps (CCC) barracks in Connecticut, preserved as a museum dedicated to this Depression-era organization.

11. Fox Hill Tower

A five-mile drive westward to Rockville brings you to Fox Hill, where an exceptional view of the Connecticut River Valley can be enjoyed at this historic site.

The initial structure at Fox Hill was a wooden observation tower erected in the 1870s, which succumbed to a blizzard in 1880 and subsequently deteriorated over the following decades.

A new octagonal stone edifice was completed by the Works Progress Administration in 1939 during the Great Depression, serving as an employment initiative.

This 22-meter monument, alongside its 67-meter promenade, honors veterans from all wars representing the town of Vernon.

Near the apex lies an observation platform from which the Metacomet Ridge’s Talcott Mountain, Mount Holyoke, and Mount Tom can all be seen across the valley on clear days.

12. Nye-Holman State Forest

This 50-acre expanse along the banks of the Willimantic River features riverside meadows and sloping woodlands, allowing for leisurely walks.

In 1720, this land was allocated to one Ebenezer Nye for the establishment of a homestead and toll bridge across the river.

This tract was farmed by six generations of the same family until Nye’s great, great, great granddaughter, Alice Holman Hall, donated it to the state in 1931. From the forest’s gravel road, an unmarked trail extends half a mile along the riverbank, flanked by ferns and wildflowers during spring and summer.

This section of the Willimantic is designated for trout management, favored by anglers for catch-and-release fly fishing.

13. Stafford Motor Speedway

There comes a time when high-speed action is desired, and the Stafford Motor Speedway, located a few miles away, is the ideal venue to fulfill that thrill.

Before automobile racing became the norm, this site functioned as a horse racetrack, established in 1870. Stafford Motor Speedway is recognized as an accredited NASCAR Whelen All-American track, hosting three Whelen modified tour events annually from May to September.

On weekends where the tour is not in session, heart-pounding races occur for various modified stock car divisions each Friday night, with accommodation for up to 8,000 spectators ensuring a good view.

14. John Cady House

As you navigate through rural Tolland, you will encounter an architecturally significant building at the intersection of Mile Hill Road and Cedar Swamp Road.

This is the John Cady House (circa 1720), believed to have been constructed by the elder John Cady, who migrated from Massachusetts—this influences its resemblance to Georgian Colonial homes found in that neighboring state rather than in Connecticut.

This 2.5-story, five-bay wide wooden structure features a portal framed by Greek Revival pilasters.

An intriguing aspect is that what is presently designated as Mile Hill Road was realigned in the late 18th century from the property’s west side to the east. In the late 1700s, the John Cady House operated as a tavern.

Although this house remains private property, it is still worthy of attention as you pass by.

15. William Benton Museum of Art

In close proximity, the Storrs campus of the University of Connecticut is home to a prestigious art museum named after the university’s former trustee and Connecticut senator.

Established in 1967, the Benton Museum is housed in a building constructed in 1920, initially serving as the university’s main dining hall.

The museum’s collection has expanded to encompass over 6,500 pieces since its inception.

Notably, the collection emphasizes American art, showcasing works by artists such as Childe Hassam, Emil Carlson, Mary Cassatt, Edward Burne-Jones, and Ellen Emmet Rand, while also featuring pieces by renowned artists such as Gustav Klimt and Käthe Kollwitz.

In autumn 2019, captivating temporary exhibitions highlighted the tropical watercolors of Reginald Marsh and African art acquired by former Professor Emeritus of Sociology Josef Gugler and his wife, Janine Gugler.