15 Best Things to Do in Simsbury (CT)

This small town west of Hartford has an impossibly beautiful location, embedded in the Farmington River Valley up against the Metacomet Ridge.

The ample woodland and majestic overlooks combine to make Simsbury one of my favorite places to experience Connecticut’s foliage in fall.

Heublein Tower, constructed for a wealthy businessman more than a century ago, is both a monument to behold and an awesome vantage point. This landmark takes in a huge slice of New England atop Talcott Mountain.

Simsbury has a long history, going back to the 1670s, with properties dating back to this time in the historic center.

Something that puts the town on the map today is the state-of-the-art Simsbury Meadows Performing Arts Center amphitheater. This home to the Hartford Symphony Orchestra for the Talcott Mountain Music Festival in summer.

1. Heublein Tower

In the 1910s the beverage magnate Gilbert F. Heublein built himself a summer retreat in the shape of a Bavarian castle.

Posted atop Talcott Mountain on the Metacomet Ridge at a height of 950 feet, the Heublein Tower cuts a familiar shape on the horizon west of Hartford.

The tower is 164 feet tall and was designed to be able to withstand winds of 100 mph.

You can reach this landmark on a yellow-blazed hiking loop from the parking lot on Summit Ridge Drive. The hike is about 1.25 miles in length and took me just over half an hour to complete.

Heublein Tower is open between Memorial Day weekend and the end of October, generally Thursday through Monday.

There are extended opening times in October when the tower affords sensational panoramas of the fall foliage. In this month you can visit every day of the week except Tuesday.

A massive swath of Connecticut rolls out before you at the observation platform. I could see from Long Island Sound, up past the Hartford skyline, as far as Mount Monadnock, 80 miles to the northeast in New Hampshire.

2. Talcott Mountain State Park

The state park below protects more than 500 acres of wilderness on the linear Metacomet Ridge.

This traprock fault, 100 miles long, runs north to south through Connecticut from Long Island Sound all the way to the Massachusetts-Vermont border.

Talcott Mountain is 13 miles in length and as with other landforms on the ridge has some unusual plant species. These thrive on the hot, dry ridges, with chestnut oaks and eastern red cedar on the barren cliff edges.

Within the park are two waterfalls, a highland swamp boardwalk and large bodies of water. Best of all for me are cliff-top views over the countryside to the west, absolutely sublime in fall.

The 50-mile Blue-Blazed Metacomet Trail traces the ridge of Talcott Mountain. This trail mostly runs parallel to the yellow trail up to Heublein Tower.

3. Old Drake Hill Flower Bridge

There’s a stirring piece of heritage crossing the Farmington River Simsbury, in the form of a steel Parker truss bridge constructed in 1892. This is one of only three bridges of its kind still intact in the state, with a span of 174 feet and a roadway 12 feet wide.

When a new two-lane bridge opened in 1992 the Old Drake Hill Bridge became a footbridge. A couple of years later it was spruced up with flower gardens growing annuals and perennials at each end.

I’m smitten with the flower boxes flanking the roadway, and you can stop for a picnic at the little park by the riverbank.

Understandably, the Flower Bridge has become an icon for Simsbury. It’s a treasured backdrop for wedding photos, and a vantage point for crew boat races on the river.

4. Simsbury Historical Society

In the heart of the town at 800 Hopmeadow Street, the Simsbury Historical Society is on a two-acre plot preserving 16 historic buildings in neat gardens.

The grounds and gardens are constantly open for you to look around, while guided tours of the showpiece Phelps Tavern are given Thursday to Saturday at 1:00 PM and 2:30 PM.

These begin at the modern Ellsworth Visitors Center, which was raised in 1966. In this building there are also interesting rotating exhibitions sourced from the society’s collections.

I saw furniture, decorative arts, textiles, costumes, paintings and objects relating to Simsbury’s Ensign-Bickford Company. This firm was once a leading manufacturer of fuses and blasting products.

Also at the Visitors Center is a play area for wee ones, with vintage wooden toys and period costume to dress up in.

5. Phelps Tavern

The main attraction at the Simsbury Historical Society is this house and tavern dating back to 1711 and expanded 70 years later.

The property was owned by the Phelps family for five generations over 200 years, but is named for Captain Elisha Phelps. Visiting here, I learned that he played a role in the Capture of Fort Ticonderoga in 1775.

The tavern was in business from around 1786 to 1849, and was donated to the Simsbury Historical Society by Mary Phelps Ensign Lovejoy in 1962.

You’ll go back to the tavern days inside, checking out a series of period rooms combined with interactive exhibits. These offer broader details about the role of taverns in New England in the 18th and 19th centuries.

6. Simsbury Center Historic District

One of my favorite things to do in old New England towns is exploring old town centers. Here, seven blocks of Hopmeadow Street are designated a Historic District, taking up more than 70 acres.

This includes the Simsbury Historical Society, along with a host of other monuments. These range in style from Colonial to Early Republic, Late Victorian and 20th-century Colonial Revival.

Some of the contributing buildings are the Simsbury Free Library (1887), the Colonial Revival Eno Memorial Hall (1932) and the First Church of Christ. The latter has been standing here in some form since 1697.

At Railroad and Station Streets, the Simsbury Railroad Depot dates from 1875 and bears some of the Italianate flourishes that were fashionable at the time.

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

7. Stratton Brook State Park

Some 30 years ago Stratton Brook State Park became the first state park in Connecticut to be made completely accessible to people with wheelchairs.

In June, July and August people descend on the park to swim in the pond on the brook and take picnics under the surrounding white pines.

There’s a bikeway here on the railbed of an old demonstration railroad, traveling across picturesque little streams.

I’d take the chance to check out the Massacoe Forest Pavilion. This was constructed in 1935 by the Civilian Conservation Corps, a voluntary public work relief program.

Fishing is available year round, and when the park’s trails are snowed over they’re adapted for cross-country skiing.

8. Rosedale Farms & Vineyards

Now into its fifth generation, this farm has been growing top-quality produce for more than a century.

It would be impossible for me to list all of the fruit and vegetables available seasonally at the farm stand. But, for the briefest summary, there’s rhubarb, berries, carrots, cucumber, eggplants, peppers, potatoes, pumpkins, broccoli, peaches, watermelon, and cantaloupe.

In summer there’s a sunflower maze to solve, and the stand has a range of delicious pies baked from scratch using ingredients from the farm.

The vineyards grow a range of vinifera and hybrid grapes for award-winning wines. Red grapes include Marquette, St. Croix, Merlot, Pinot Noir and Sangiovese, and among the whites are Bianca, Meynieu, Seyval Blanc, Chardonnay and Traminette

You can stop by all summer up to the end of October to enjoy a bottle paired with local cheese or treats from the farm stand.

9. Simsbury Celebrates

Every year, Simsbury gets into the holiday spirit with this one-day town-wide event. I’d check the schedule in advance because there’s so much going on in a relatively short space of time.

I’m talking ice sculpting, trolley rides, a live nativity, selfies with Santa, painted sleighs, a holiday cabaret, and lots of delicious festive food.

There performances to catch at various venues, from a charming children’s singalong to a show by the Modern Vintage Opera.

The whole event builds up to a parade of decorated fire trucks followed by a fireworks show at Simsbury Meadows Performing Arts Center.

10. Pinchot Sycamore

Near the foot of Talcott Mountain on the east bank of the Farmington River grows the largest tree in the state of Connecticut.

When it was last measured in 2016 by the Connecticut Botanical Society this monumental American sycamore had a trunk 28+ feet in circumference with a height of 100 feet. Meanwhile, the canopy diameter was a little less than 131 feet

The tree is named in tribute to Gifford Pinchot (1865-1946), a leading figure in conservation in Connecticut and the United States.

The tree is thought to be at least 200, but is possibly more than 300 years old. I love the little park encompassing the tree, and it’s a fine place to launch a kayak on the Farmington River.

11. Simsbury Meadows Performing Arts Center

Out in the bucolic Farmington Valley countryside is a state-of-the-art outdoor venue for concerts under the night sky.

This is the second-largest outdoor stage in Connecticut, with a capacity of 10,000. The Hartford Symphony Orchestra relocates to Simsbury Meadows in the months of June and July, in time for the Talcott Mountain Music Festival.

Meanwhile a whole spectrum of contemporary artists takes the stage for a Summer Concert Series between June and September.

Also, Septemberfest is a family event now deep into its fourth decade. During this shindig you’ve got food trucks, and a whole program of live music over three evenings.

12. Bicycling

Simsbury has been designated a Bicycle Friendly Community by the League of American Cyclists. I could spend days pedaling along quiet town roads or traffic-free greenways like the Farmington Canal Heritage Trail.

This route is on the course of a canal turned railroad in the first decades of the 19th century to link New Haven with Connecticut and New England’s interior.

Simsbury has plotted a scenic 14-mile sharrowed loop that you can find on the Town of Simsbury website.

It’s also no trouble to rent or borrow a bicycle here. You can get hold of a pair of wheels for a day or more at the Bicycle Cellar (532 Hopmeadow St).

13. Flamig Farm

On Shingle Mill Rd, I doubt you’ll miss this place thanks to the enormous sign spelling “EGGS” backwards on its barn.

Flamig Farm has a history dating back to 1907, and this plot of land has been put to many different uses over the last 115+ years.

Nowadays, the farm store is open April through November, selling eggs of course, as well as a range of handmade toys and clothing. In the summer, Flamig Farm is also a visitor attraction for littler family members.

There’s a petting zoo with all sorts of cute animals, like goats, ponies, miniature horses, llamas, alpacas, turkeys, potbellied pigs, and rabbits.

Kids can also take pony rides, while families can even book a stay at the farm’s cozy lodgings.

Flamig Farm is famous for its spooky Halloween hayrides, and springs to life again in the build-up to Christmas when Santa calls in.

14. Roaring Brook Nature Center

This nature museum and sanctuary first opened as long ago as 1948. In the 1960s the property was gifted the adjacent Werner Farm, over 100 acres.

At Roaring Brook you can peruse permanent and changing exhibits on the local landscape and wildlife. There’s also a replica Eastern Woodland Native American longhouse, and a beaver wetland exhibit, which I adored.

The center keeps a small collection of animals, like birds in outdoor free-flight aviaries. Meanwhile the colorful outdoor gardens are alive with wildflowers, butterflies and birds in spring and summer.

Roaring Brook also looks after five miles of trails disappearing into the neighboring Werner’s Woods. You can get hold of trail maps and a wildlife checklist at the center’s store.

As for programs, there are “Discovery Days” tailored for students, seasonal guided nature walks for all ages, as well as summer concerts and a “Hobgoblin Fair” at Halloween.

15. Simsbury Farms Golf Course

You’ll have to travel a long way to find a public course as good as Simsbury Farms. These 18 holes are regarded as some of the best in the region by the New England Journal of Golf.

The course was plotted on the site of a former orchard at the turn of 1970s by renowned architect Geoffrey Cornish. I have to say, the roller coaster terrain caught me by surprise with some striking views.

With its sharp elevation changes, narrow fairways, water and bunkers, Simsbury Farms poses a challenge for golfers of all levels. Complementing the track is a clubhouse from the 2010s, a generous practice green, and a driving range.