Old Drake Hill Flower Bridge is a bridge in Simsbury, Connecticut.

This Is The Friendliest Small Town in Connecticut

Simsbury's roots date back to the mid-17th century when it was settled as one of the first western outposts beyond the Connecticut River Valley. Its strong sense of patriotism was evident during the Revolutionary War, with nearly 1,000 residents stepping up to serve in support of the young country. That same pioneering spirit persists today, with a tight-knit community that thrives through rural farming traditions and local support for the arts and culinary scene. Are you looking for a place in Connecticut where community spirit shines? You will find it in the friendly town of Simsbury.

Farming and Agricultural Community

Aerial view of the tower sits on the Talcott Mountain State Park in Simsbury, Connecticut.
Talcott Mountain State Park in Simsbury, Connecticut.

Simsbury, located in northcentral Connecticut, is home to a thriving agricultural community, with more than ten farms scattered throughout the surrounding areas. Many of the farms welcome visitors, eager to share some of their agricultural traditions. Rosedale Farms and Vineyards, a fifth-generation family farm, is an excellent destination for visitors. They sell fresh produce, flowers, and wines, along with hosting a variety of seasonal events. In the fall, guests can enjoy activities like a sunflower stroll, farm fest, and corn maze. In the warmer months, the farm also hosts chef-to-farm dinners that consist of a chef-designed, six-course feast. Make sure to stop by the farm on the weekends to enjoy live music in the afternoons!

Rosedale Farm and Vineyard, Simsbury, Connecticut.
Rosedale Farm and Vineyard, Simsbury, Connecticut. Image credit Blake via Flickr.com

Whether travelers are new riders or more experienced, Folly Farm Show Stables is a wonderful place to spend an afternoon horseback riding. This farm, which the Patricelli Family has owned for over 40 years, is situated at the foot of Talcott Mountain and spans 175 acres. Friendly instructors offer visitors the chance to learn about the horses and go horseback riding, appreciating the gorgeous countryside.

From April through November, Flamig Farm is popular with families and includes a farm animal petting zoo. Some of the animals children can interact with and feed include pigs, chickens, goats, rabbits, turkeys, ponies, donkeys, peacocks, cows, and sheep. Visitors can also enjoy pony rides and tractor rides!

Performing Arts

Simsbury Meadows Performing Arts Center.
Simsbury Meadows Performing Arts Center, Connecticut. Image credit Jon / Matt Phillips via Flickr.com

Simsbury’s residents have a deep appreciation for the arts, with numerous opportunities to enjoy live music and theater performances. Each summer, the Hartford Symphony Orchestra makes the Simsbury Performing Arts Center its home for the Talcott Mountain Music Festival. This summer series features five concerts, allowing visitors to relax on the lawn while enjoying the music. The festival's highlight is the special 'Celebrate America!' concert on the 4th of July, which concludes with a fireworks display.

The Simsbury Light Opera Company, a community-based nonprofit, performs regularly in Simsbury as well. The company specializes in Gilbert and Sullivan operettas while also presenting light operas from other composers each spring. There are several other venues to check out for live band performances! Some of the beloved venues in town include the Old Well Tavern, LittleHouse Live, and the Maple Tree Cafe.

Outdoor Recreation

Stratton State Park is a great recreational venue near Simsbury, Connecticut.
Stratton State Park is a great recreational venue near Simsbury, Connecticut.

With 10 municipal parks and four state-run parks, Simsbury has plenty of opportunities for residents and visitors to enjoy the outdoors with family and friends. Stratton Brook State Park, established as a state park in 1949, is a great spot for a day outdoors. In 1996, it became the first fully wheelchair-accessible state park in Connecticut. Bikers can also explore a trail that winds past white pines, scenic brooks, and a covered bridge. The park additionally provides opportunities for swimming, fishing, and picnicking.

Sycamore tree located in Simsbury, Connecticut.
Sycamore Tree in Simsbury, Connecticut. Image credit Marty Aligata, CC BY-SA 4.0, via Wikimedia Commons

The Pinchot Sycamore is a popular picnicking site, home to the oldest and largest tree in the state, standing around 100 feet tall with a circumference of over 28 feet. Located near the Farmington River, this spot not only offers a nice place to relax in the tree's shade but also serves as a launch site for kayaks and canoes.

Culinary Scene

Benny's, Simsbury Connecticut
Benny's, Simsbury, Connecticut. Image credit John Phelan, CC BY 4.0, via Wikimedia Commons

On any given weekend in Simsbury, the local restaurants are filled with people eager to enjoy a meal in good company. Millwright's Restaurant, one of the highest-rated in town, serves innovative dishes crafted by Chef Tyler Anderson. The restaurant features three dining areas: The Dining Room, a formal space with floor-to-ceiling windows offering views of the falls; The Tavern, a cozy, casual setting with stone walls and a welcoming chimney; and The Loft, an intimate event space with a private entrance, accommodating 10 to 40 guests.

Plan b Burger Bar Simsbury is another highly recommended dining option. This burger bar serves burgers made from 100% Certified Black Angus beef, sourced from Midwest ranchers. It also has 14 rotating drafts and a selection of high-quality bourbons, perfectly complementing your meal.

Although there are many historic towns in New England and Connecticut, Simsbury’s strong sense of patriotism and community involvement truly sets it apart from the rest. The town’s community opera companies, family-owned horse stables, fall farm festivals, and hole-in-the-wall music venues are just a few parts of the friendly community that has a way of bringing people together. By the time you finish your tour of Simsbury, you will feel right at home, just like one of the locals!

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