Top 15 Attractions and Activities in Simsbury, Connecticut

Summary

Heublein Tower
Talcott Mountain State Park
Old Drake Hill Flower Bridge
Simsbury Historical Society
Phelps Tavern
Simsbury Center Historic District
Stratton Brook State Park
Rosedale Farms & Vineyards
Simsbury Celebrates
Pinchot Sycamore
Simsbury Meadows Performing Arts Center
Bicycling
Flamig Farm
Roaring Brook Nature Center
Simsbury Farms Golf Course

This small town west of Hartford is set in an extraordinarily attractive location, nestled within the Farmington River Valley at the base of the Metacomet Ridge.

The plentiful woodlands and breathtaking overlooks contribute to making Simsbury one of my preferred locations to observe Connecticut’s autumn foliage.

Heublein Tower, erected for a prosperous businessman over a century ago, serves both as a remarkable monument and a splendid observation point. This landmark provides expansive views of New England from the summit of Talcott Mountain.

Simsbury has a rich history, stretching back to the 1670s, with structures from this period preserved in the historic center.

Significantly enhancing the town’s profile today is the contemporary Simsbury Meadows Performing Arts Center amphitheater. This venue hosts the Hartford Symphony Orchestra during the Talcott Mountain Music Festival each summer.

1. Heublein Tower

In the 1910s, beverage tycoon Gilbert F. Heublein constructed a summer residence designed in the style of a Bavarian castle.

Perched atop Talcott Mountain on the Metacomet Ridge at an elevation of 950 feet, the Heublein Tower stands as a prominent silhouette on the horizon west of Hartford.

The tower rises to a height of 164 feet and was engineered to endure winds of up to 100 mph.

This landmark can be accessed via a yellow-blazed hiking loop originating from the parking area on Summit Ridge Drive. The hike spans approximately 1.25 miles and I completed it in just over half an hour.

Heublein Tower is accessible from Memorial Day weekend until the end of October, typically from Thursday to Monday.

There are extended operating hours in October, during which visitors can enjoy stunning views of the fall foliage. In this month, the tower is open daily, except on Tuesdays.

A vast expanse of Connecticut stretches before you from the observation platform. On clear days, one can see from Long Island Sound, past the Hartford skyline, as far as Mount Monadnock, located 80 miles to the northeast in New Hampshire.

2. Talcott Mountain State Park

The state park encompasses more than 500 acres of protected wilderness along the linear Metacomet Ridge.

This traprock fault, which extends 100 miles from north to south across Connecticut, stretches from Long Island Sound to the Massachusetts-Vermont border.

Talcott Mountain spans 13 miles and, like other geographical features along the ridge, hosts some rare plant species. These species thrive in the warm, dry conditions, including chestnut oaks and eastern red cedar growing on the steep cliffs.

The park contains two waterfalls, a highland swamp boardwalk, and several large bodies of water. The cliff-top views of the countryside to the west are particularly breathtaking, especially during the fall season.

The 50-mile Blue-Blazed Metacomet Trail follows the ridge of Talcott Mountain, running parallel to the yellow trail leading to Heublein Tower.

3. Old Drake Hill Flower Bridge

A piece of history adorns the Farmington River in Simsbury, encapsulated by the steel Parker truss bridge built in 1892. This bridge is one of only three of its kind still standing in the state, boasting a span of 174 feet and a roadway width of 12 feet.

Upon the opening of a new two-lane bridge in 1992, the Old Drake Hill Bridge transitioned to a pedestrian bridge. Several years later, it was adorned with flower gardens featuring annuals and perennials at both ends.

The flower boxes lining the roadway have captivated me, and there is an inviting little park by the riverbank, ideal for a picnic.

As a result, the Flower Bridge has become a symbol of Simsbury, serving as a cherished backdrop for wedding photos and a viewpoint for crew boat races conducted on the river.

4. Simsbury Historical Society

Located in the town center at 800 Hopmeadow Street, the Simsbury Historical Society occupies a two-acre estate containing 16 historic structures within beautifully maintained gardens.

The grounds and gardens are open to the public for exploration, while guided tours of the prominent Phelps Tavern are offered Thursday through Saturday at 1:00 PM and 2:30 PM.

These tours commence at the modern Ellsworth Visitors Center, established in 1966, which features intriguing rotating exhibits sourced from the society’s collections.

Visitors can view artifacts including furniture, decorative arts, textiles, costumes, paintings, and items related to Simsbury’s Ensign-Bickford Company, once a leading producer of fuses and blasting products.

The Visitors Center also includes a play area for young children, featuring vintage wooden toys and period costumes for dress-up.

5. Phelps Tavern

The highlight of the Simsbury Historical Society is this tavern and residence dating back to 1711, which underwent expansion 70 years later.

Owned by the Phelps family for five generations over two centuries, it is named after Captain Elisha Phelps, who played a role in the Capture of Fort Ticonderoga in 1775.

The tavern operated from approximately 1786 to 1849 and was bequeathed to the Simsbury Historical Society by Mary Phelps Ensign Lovejoy in 1962.

Within, visitors can immerse themselves in the tavern’s historical atmosphere, exploring a series of period rooms alongside interactive exhibits that elaborate on the function of taverns in New England during the 18th and 19th centuries.

6. Simsbury Center Historic District

Exploring historic town centers in New England is one of my preferred activities, and in Simsbury, seven blocks of Hopmeadow Street are designated as a Historic District, encompassing over 70 acres.

This area includes the Simsbury Historical Society alongside numerous other monuments that exemplify various architectural styles, from Colonial to Early Republic, Late Victorian, and 20th-century Colonial Revival.

The district features notable buildings such as the Simsbury Free Library (1887), the Colonial Revival Eno Memorial Hall (1932), and the First Church of Christ, which has been established in some form since 1697.

At the intersection of Railroad and Station Streets, the Simsbury Railroad Depot traces back to 1875 and exhibits some Italianate embellishments that were popular at that time.

The oldest site is Simsbury Cemetery at 755, founded in 1688 on the original site of the town’s first meeting house.

7. Stratton Brook State Park

Approximately 30 years ago, Stratton Brook State Park became the first state park in Connecticut fully accessible to individuals with disabilities.

During the months of June, July, and August, visitors flock to the park to swim in the pond and enjoy picnics beneath the surrounding white pines.

Here, a bikeway runs along the route of a former demonstration railroad, winding through picturesque streams.

I recommend visiting the Massacoe Forest Pavilion, built in 1935 by the Civilian Conservation Corps, a public work relief initiative.

Fishing is permitted year-round, and during snowy months, the park’s trails are adapted for cross-country skiing.

8. Rosedale Farms & Vineyards

Now in its fifth generation, this farm has been cultivating high-quality produce for over a century.

It would be challenging to list all the seasonal fruits and vegetables available at the farm stand, but to summarize briefly, options include rhubarb, berries, carrots, cucumbers, eggplants, peppers, potatoes, pumpkins, broccoli, peaches, watermelon, and cantaloupe.

In summer, a sunflower maze invites exploration, and the stand features an assortment of delicious pies made from scratch using farm-sourced ingredients.

The vineyards produce a variety of vinifera and hybrid grapes, resulting in award-winning wines. Varietals include red grapes such as Marquette, St. Croix, Merlot, Pinot Noir, and Sangiovese, along with white varieties like Bianca, Meynieu, Seyval Blanc, Chardonnay, and Traminette.

Visitors can enjoy a bottle of wine paired with local cheese or treats from the farm stand throughout the summer until the end of October.

9. Simsbury Celebrates

Each year, Simsbury embraces the holiday spirit with a one-day, town-wide celebration. It is advisable to review the schedule in advance, as numerous activities take place in a relatively short timeframe.

The event features ice sculpting, trolley rides, a live nativity scene, photo opportunities with Santa, decorated sleighs, a holiday cabaret, and a delectable assortment of festive food.

Various performances occur at multiple venues, ranging from a delightful children’s singalong to a presentation by the Modern Vintage Opera.

The festivities culminate in a parade of decorated fire trucks, followed by a fireworks display at Simsbury Meadows Performing Arts Center.

10. Pinchot Sycamore

At the base of Talcott Mountain, on the east bank of the Farmington River, stands the largest tree in Connecticut.

In 2016, the Connecticut Botanical Society last measured this extraordinary American sycamore, which had a trunk circumference exceeding 28 feet and a height of 100 feet, with a canopy diameter nearing 131 feet.

The tree, named in honor of Gifford Pinchot (1865-1946), a prominent advocate for conservation in Connecticut and throughout the United States, is believed to be at least 200 years old, and possibly over 300 years old.

The surrounding park, which encompasses the tree, offers a pleasant area to launch a kayak on the Farmington River.

11. Simsbury Meadows Performing Arts Center

Set against the picturesque backdrop of the Farmington Valley, this state-of-the-art outdoor venue hosts concerts beneath the stars.

This represents the second-largest outdoor stage in Connecticut, accommodating up to 10,000 attendees. The Hartford Symphony Orchestra performs at Simsbury Meadows during June and July as part of the Talcott Mountain Music Festival.

A diverse array of contemporary artists also graces the stage during the Summer Concert Series, which runs from June to September.

Additionally, Septemberfest has evolved into a family friendly celebration now in its fourth decade, marked by food trucks and live entertainment spanning three evenings.

12. Bicycling

Simsbury has been recognized as a Bicycle Friendly Community by the League of American Cyclists. You can spend days cycling along tranquil town roads or on traffic-free greenways like the Farmington Canal Heritage Trail.

This route follows the path of a canal converted into a railway in the early 19th century, which connected New Haven with Connecticut and New England’s interior.

A scenic loop encompassing 14 miles has been outlined for cyclists, available on the Town of Simsbury’s website.

Renting or borrowing a bicycle is straightforward; you can acquire a bike for a day or longer at the Bicycle Cellar (532 Hopmeadow St).

13. Flamig Farm

Located on Shingle Mill Rd, you will likely notice this establishment due to its enormous sign, which spells “EGGS” backwards on the barn.

Founded in 1907, Flamig Farm has experienced diverse uses over its 115+ years of existence.

Currently, the farm store operates from April through November, offering not only eggs but also a selection of handcrafted toys and clothing. During the summer, Flamig Farm is also a popular destination for families with children.

The petting zoo features a variety of animals including goats, ponies, miniature horses, llamas, alpacas, turkeys, potbellied pigs, and rabbits.

Children can enjoy pony rides, while families may even spend the night at the farm’s cozy accommodations.

Flamig Farm is celebrated for its spooky Halloween hayrides and becomes particularly lively during the Christmas season when Santa makes an appearance.

14. Roaring Brook Nature Center

This nature museum and sanctuary first opened its doors in 1948. In the 1960s, the property expanded to include the adjacent Werner Farm, encompassing over 100 acres.

At Roaring Brook, visitors can explore both permanent and changing exhibits focusing on the local landscape and wildlife. A replica of an Eastern Woodland Native American longhouse and a beaver wetland exhibit are additional highlights that I particularly enjoyed.

The center also maintains a small collection of animals, such as birds in outdoor free-flight aviaries. Meanwhile, the vibrant outdoor gardens are filled with wildflowers, butterflies, and birds during spring and summer.

Roaring Brook also manages five miles of trails that meander into the neighboring Werner’s Woods, where trail maps and a wildlife checklist can be acquired at the center’s store.

Moreover, various programs are available, including “Discovery Days” designed for students, seasonal guided nature walks, summer concerts, and a “Hobgoblin Fair” during Halloween.

15. Simsbury Farms Golf Course

Finding a public golf course as exceptional as Simsbury Farms is quite a challenge. These 18 holes are regarded as some of the finest in the region, as noted by the New England Journal of Golf.

The course was designed on the site of a former orchard in the early 1970s by renowned architect Geoffrey Cornish. The exciting terrain, with its significant elevation shifts, surprised me with wonderful views.

Characterized by its sharp elevation changes, narrow fairways, water hazards, and bunkers, Simsbury Farms presents a challenge for golfers of varying skill levels. The facility features a contemporary clubhouse along with a spacious practice green and a driving range.

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