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Need a peaceful New England retreat filled with nature and charm? Head to Simsbury! Tucked in the Farmington Valley, Simsbury is known for its scenic beauty, colonial charm, and vibrant outdoor life. Whether you’re biking along the river or savoring farm-to-table meals, Simsbury delivers small-town warmth with big appeal year-round.

Simsbury, CT Highlights:

  • For Outdoor Enthusiasts: Bike the Farmington Canal Heritage Trail – Ride or stroll along this scenic rail trail with views of woods, rivers, and bridges.
  • For History Buffs: Tour the Phelps Tavern Museum – Step back into 18th-century life at this well-preserved colonial inn.
  • For Shoppers: Explore Simsbury Town Center and local farm stores – Discover boutique shops, art galleries, and local markets.
  • For Couples: Dine and unwind at Millwright’s Restaurant – A romantic meal overlooking a waterfall in a restored 17th-century mill.
  • For Families: Climb and play at Talcott Mountain State Park – Hike to Heublein Tower for panoramic views and picnic-ready green space.

Best Time to Visit Simsbury, CT

The best time to visit Simsbury is during spring (April–June) and fall (September–October). Expect colorful blooms or breathtaking foliage, ideal weather for hiking and festivals. Winter is peaceful and cozy, while summer offers outdoor concerts and farmer’s markets.

How to Get to Simsbury, CT

  • If you are traveling by car: Simsbury is accessible via Route 10 and Route 44, just 30 minutes northwest of Hartford and under 2 hours from Boston.
  • By Plane: Bradley International Airport (BDL) is only 25 minutes away and offers flights from major U.S. cities.
  • By Train: Amtrak service is available in nearby Hartford or Windsor Locks, with car rentals for local travel.

Where to Stay in Simsbury, CT

  • Recommended for Families: Simsbury Inn – Elegant New England charm with an indoor pool, on-site dining, and mountain views.
  • For Couples: Green Acres Bed & Breakfast – Cozy, romantic farm-style inn with personal service and rustic charm.
  • For Boutique Vibes: Iron Horse Inn – Affordable comfort with easy access to downtown shops and the bike trail.

Best Things to Do in Simsbury, CT

1. Talcott Mountain State Park

Talcott Mountain State Park

© ondreicka/stock.adobe.com

Located on Talcott Mountain in the towns of Avon, Bloomfield, and Simsbury, the Talcott Mountain State Park is a 574-acre public park and recreation with several attractions, including the 165-foot-high mountaintop lookout known as Heublein Tower.

The former summer home of a prominent Hartford family and familiar Farmington River Valley landmark, Heublein Tower features a local history museum and charming picnic areas. The surrounding park features several hiking and walking trails and is home to a diverse array of fauna and flora, such as bald eagles, turkey vultures, pileated woodpeckers, and beautiful wildflowers. There are also restrooms, picnic tables and grills for visitors.

Summit Ridge Dr, Simsbury, CT 06070, USA, Phone: 860-242-1158

2. Heublein Tower


Climb to the top and admire historic sights on a fun fall outing.

Heublein Tower

© Heublein Tower

The Heublein Tower is a historic hilltop in Simsbury, Connecticut that provides spectacular panoramic views of the Farmington River Valley and the Hartford skyline.

We definitely recommend stopping here if love a good view! Built in 1914, the European-styled tower was designed by manufacturing magnate Gilbert Heublein as a summer retreat for his family after romantically promising his wife he would build her a castle on a hill one day. Designed in a Bavarian style, the 165-foot tall tower was built to withstand the high winds that assailed the peak with a quartet of massive steel girders around its base.

It also featured the first elevator in the state. Today, the 165-foot-high mountaintop lookout and familiar Farmington River Valley landmark features a local history museum and charming picnic areas for visitors. The Heublein Tower can be reached by a pleasant 1.25-mile hike.

Simsbury, CT 06070, Phone: 860-242-1158

Attractions for Couples

3. Rosedale Farms & Vineyards


Sip local wines and enjoy a romantic stroll through vineyard views.

Rosedale Farms & Vineyards

© Rosedale Farms & Vineyards

Rosedale Farms & Vineyards is a fifth-generation family farm that produces fresh fruits, vegetables, flowers and organic wines.

Established in 1920, the family-owned and operated farm is located in the heart of Simsbury and has been providing the community with the freshest, highest-quality produce and friendliest service ever since.

Rosedale Farms & Vineyards offers memberships which include the purchase of fresh fruit, vegetables, herbs and flowers, and organically produced wines, and visitors to the farm can sample the award-winning wines paired with crackers, cheese and fresh pastries on the farmhouse patio.

25 E Weatogue St, Simsbury, CT 06070, Phone: 860-651-3926

4. Old Drake Hill Flower Bridge


Walk across blooms and admire this unusual and charming landmark.

Old Drake Hill Flower Bridge

© Old Drake Hill Flower Bridge

The Old Drake Hill Flower Bridge, also known as the Drake Hill Road Bridge is a scenic bridge of flowers across the Farmington River.

Built in 1892 to carry Drake Hill Road over the Farmington River, the Old Drake Hill Flower Bridge is one of three Parker truss bridges left in the state and listed on the National Register of Historic Places. Today, the single-span, pin-connected Parker through truss bridge is open to pedestrian and bicycle traffic only with a wooden plank deck suitable for pedestrians and is adorned with planters that are seasonally filled with flowers. Visit in the spring and admire the flowers!

Drake Hill Road, Simsbury, CT 06070, Phone: 860-658-3255

5. Stratton Brook State Park


Swim, bike, and enjoy a family-friendly weekend full of outdoor fun.

Stratton Brook State Park

© buharina/stock.adobe.com

The Stratton Brook State Park is a state park and public recreation area that offers a range of outdoor recreational activities such as hiking, fishing, boating, swimming, mountain biking, cross-country skiing, and ice-skating in winter.

A seasonal nature center provides extensive information on the park and the fauna and flora that can be found within it, as well as several annual interpretive programs that are conducted in the beautifully wooded setting of the park. Other notable features include the Massaco Forest Pavilion, which was built by the Civilian Conservation Corps in 1935 and amenities in the park include picnic shelters with tables and benches and modern restrooms.

149 Farms Village Road, Simsbury, CT 06070, Phone: 860-658-1388

7. Millwrights


Dine beside a waterfall and savor a romantic fine dining experience.

Millwrights

© Millwrights

Perched atop a waterfall in Simsbury, Millwrights is an elegant restaurant based in a 17th-century mill that serves an award-winning menu created by acclaimed, James Beard nominated Chef Tyler Anderson and his team.

Boasting a beautiful plank-ceilinged room with waterfall views and a cozy basement tavern, Millwright’s offers a new experience to the Farmington Valley farm-to-table dining scene with cuisine prepared with the freshest; high quality curated farm ingredients. The award-winning cuisine is accompanied by fine wines from around the world, and proprietary cocktails and after-dinner drinks can be enjoyed in the basement tavern’s intimate crafted bar which has a large stone fireplace and comfortable ambience. Millwrights is open for lunch on Fridays, dinner Tuesday through Friday, and Sunday brunch.

77 West St, Simsbury, CT 06070, Phone: 860-651-5500

8. Abigail's Grille


Enjoy historic charm and savor a cozy, retirement-friendly evening out.

Abigail's Grille

© Abigail's Grille

Abigail's Grille is a colonial-era tavern and historic landmark that serves contemporary American cuisine in a cozy and casual setting.

Built during the American Revolution in 1780, this Simsbury landmark was known as The Pettibone Tavern for almost two centuries and played host to several notable guests, including George Washington who used the tavern as a meeting spot for discussing strategy and plans for the Revolution. Alternating between a local watering hole and a private residence over the decades, the landmark structure has a rich history surrounding Mrs Abigail Pettibone, and it is speculated that Abigail's ghost still roams the tavern. Abigail's Grille is open seven days a week, serving lunch and dinner daily and brunch on Sunday.

4 Hartford Rd, Weatogue, CT 06089, Phone: 860-264-1580

9. Plan B Burger Bar


Bite into bold burgers and enjoy an easy, fun stop with kids or friends.

Plan B Burger Bar

© Plan B Burger Bar

Plan B Burger Bar is a stylish chain that serves creative burgers, other elevated pub grub, and a wide range of craft beers and bourbons.

Opened in 2006, the popular eatery specializes in America’s favorite food and offers a wide range of burgers made with hand ground, antibiotic and hormone-free prime beef, fresh salads and sauces and freshly baked buns. Signature burgers include the Baja with avocado, jalapeños, jack cheese, and chipotle spread; the Squealer packed with a half-pork, half-beef burger, bacon, pickles, cheese and tomato; and Double Chili Cheese Burger with twin chuck patties, pale ale beer cheese, frizzled onions, chili, pickled jalapeño onion relish. Burgers are paired with craft beers by the bottle and on tap, a variety of artisanal bourbons.

4 Railroad St, Simsbury, CT 06070, Phone: 860-658-4477

If you are interested in local events:

  • For Music Fans: Summer Concert Series at Simsbury Meadows (June–August) – Enjoy orchestras, tribute bands, and family entertainment outdoors.
  • For Fall Fun: Simsbury Fly-In & Car Show (September) – Vintage planes, classic cars, food trucks, and local fun.
  • For Holiday Cheer: Simsbury Celebrates (November) – Fireworks, lights, carolers, and a festive town-wide holiday kickoff.

Day Trip Itineraries Within 30 Minutes of Simsbury, CT:

  • For Nature and Views: McLean Game Refuge (10–15 min) – Explore peaceful trails, woodlands, and wildlife viewing areas.
  • For Art and History: New Britain Museum of American Art (30 min) – A rich collection of American works in an engaging space.
  • For Shopping and Dining: West Hartford Center (25 min) – Trendy boutiques, top restaurants, and a walkable downtown scene.
  • For River Walks: Collinsville (20 min) – Historic mill town with cafés, kayaking, and trails along the Farmington River.
  • For Family Fun: Roaring Brook Nature Center (15 min) – Kids can meet animals, hike trails, and explore educational exhibits.

Frequently Asked Questions:

  • Q: Where is Simsbury located?
  • A: Simsbury is a town in Hartford County with a population of around 25,000.
  • Q: What is Simsbury known for?
  • A: Simsbury is home to several outstanding private schools and the Simsbury Meadows Performing Arts Center, built in 2005.
  • Q: What outdoor attractions can be found in Simsbury?
  • A: Outdoor attractions include the 574-acre Talcott Mountain State Park and the scenic Old Drake Hill Flower Bridge.
  • Q: What historical site is located in Simsbury?
  • A: Simsbury is home to the historic Phelps Tavern Museum.

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