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Craving small-town charm with colonial roots? Head to Windsor! As Connecticut’s oldest town, Windsor blends historical intrigue with riverfront recreation, local dining, and scenic New England beauty. Whether you're exploring museums, kayaking the Farmington River, or strolling a charming Main Street, Windsor is a peaceful yet engaging destination.

Windsor, CT Highlights:

  • For Families: Visit Northwest Park – Enjoy walking trails, a nature center, farm animals, and picnic spots in this 473-acre town park.
  • For Outdoor Enthusiasts: Paddle the Farmington River – Canoe or kayak through calm, scenic waters that run through Windsor.
  • For Kids: Play at the Windsor Meadows State Park – A riverside park with open space for games, biking, and scenic walks.
  • For an Adventure: Bike the Windsor River Trail – A peaceful path along the Connecticut River ideal for walking, jogging, or cycling.
  • For Shoppers: Explore downtown Windsor – Discover boutiques, historic landmarks, and locally owned cafés along the Main Street corridor.

When I like to visit Windsor, CT

The best time to visit Windsor is from late spring through early fall (May–October). These months offer warm weather for outdoor activities, blooming landscapes, and town events. Fall is especially scenic with vibrant foliage and crisp air.

My tips for getting to Windsor, CT

  • By Car: Windsor is located off I-91, just 15 minutes north of Hartford and 30 minutes south of Springfield, MA.
  • By Train: Windsor is served by Amtrak and CTrail's Hartford Line, with service to Hartford, Springfield, and New Haven.
  • By Air: Bradley International Airport (BDL) is only 10 minutes away and offers numerous domestic and limited international flights.

Where I like to stay in Windsor, CT

  • Hilton Garden Inn Hartford North/Bradley Int’l Airport – Comfortable, modern lodging with river views and free shuttle service to the airport.
  • Marriott Hartford/Windsor Airport – Full-service hotel with spacious rooms, pool, and convenient location near I-91.
  • Residence Inn by Marriott – Great for extended stays with suites and kitchenettes in a quiet, suburban setting.

Best Things to Do in Windsor, CT

1. Northwest Park


"Hike peaceful trails and visit farm animals on a relaxing family trip."

Northwest Park

© Thomas/stock.adobe.com

Northwest Park and Nature Preserve is a 473-acre community park that offers a wide variety of outdoor recreation such as hiking and walking trails, a nature center and soccer fields. Set along the Farmington River in the Poquonock section of Windsor, the municipally owned park was founded in 1972 and is currently owned and managed by the Town of Windsor and the Department of Recreation and Leisure Services. In addition to providing the community with a safe space to enjoy outdoor activities, the park also strives to be a ‘living classroom’ which showcases and conserves the natural fauna and flora of the area. The nature center offers a range of educational and nature programs, classes and workshops for visitors of all ages.

145 Lang Rd, Windsor, CT 06095, Phone: 860-285-1886

2. Vintage Radio and Communications Museum of Connecticut


"Explore old tech and discover unusual gadgets in this affordable museum stop."

Vintage Radio and Communications Museum of Connecticut

© Vintage Radio and Communications Museum of Connecticut

The Vintage Radio and Communications Museum of Connecticut is a unique institution that highlights the importance of communications and how they have helped to transform society. The museum features a fascinating collection of artifacts and objects relating to communications, including phonographs, televisions, crystals, telephones, early computers, and a variety of recording equipment. Exhibits at the museum are arranged by decade from the mid-1800s to the 1970s and feature interesting displays such as a 1940 Wurlitzer jukebox. In addition to the wonderful exhibits, volunteers offer classes on how to build and repair radios, and the facility houses a vintage broadcast studio from which an amateur radio station, W1VCM is hosted.

115 Pierson Ln, Windsor, CT 06095, Phone: 860-683-2903

Activities for Couples

3. Keney Park Golf Course


If you think like me: "Play scenic fairways and enjoy a quiet weekend round near the city."

Keney Park Golf Course

© Keney Park Golf Course

The Keney Park Golf Course is an 18-hole golf course set within Hartford's Keney Park that was designed by Devereux Emmet. A renowned name in the history of golf course architecture, Emmet designed the course in 1927 with an iconic layout which was later restored and redesigned by Milwaukee-based golf course architect Matthew Dusenberry, a longtime associate at Greg Norman Golf Course Design. Today, the course features pristine fairways, challenging greens, and bunkers, renovated tee boxes and an updated clubhouse. A Pro Shop stocks all the latest equipment and gear and golf leagues for men, women and junior golfers are hosted at the club.

171 Windsor Ave, Windsor, CT 06095, Phone: 860-543-8618

4. Windsor Historical Society


"Tour colonial homes and learn local stories on this quick educational outing."

Windsor Historical Society

© Windsor Historical Society

Windsor Historical Society is a local historical society that focuses on the collection and preservation of records, facts, and materials relating to the history of Windsor, as well as the conservation of buildings and locations of historical interest. Founded in 1921, the Society features a hands-on learning center with a permanent exhibit that documents the 400-year-old history of Windsor through an array of collections and treasures. Historic houses that fall under the Windsor Historical Society umbrella include the Strong-Howard House, the Chaffee House, and several other homes that were built before 1850, and visitors can enjoy guided tours of the houses on request.

96 Palisado Ave, Windsor, CT 06095, Phone: 860-688-3813

Recommended Activities for Families

5. Windsor Arts Center


My top 5: "Admire local exhibits and catch live performances in a charming cultural attraction."

Windsor Arts Center

© Windsor Arts Center

The Windsor Art Center is a visual and performing arts center that presents art exhibitions and musical performances by renowned and up-and-coming artists. Housed in a former freight house next to the Amtrak line in downtown Windsor, the center hosts a variety of theatrical and arts-related programs such as children’s activities, demonstrations and presentations, and artist talks, along with a calendar of seasonal programming. Entrance to the gallery is free, and a small gift shop sells locally made art, handcrafted jewelry and crafts, and unique gifts.

40 Mechanic St, Windsor, CT 06095, Phone: 860-688-2528

6. Oliver Ellsworth Homestead


I recommend: "Step into history and explore this preserved home on a quiet retirement visit."

Oliver Ellsworth Homestead

© Oliver Ellsworth Homestead

The Oliver Ellsworth Homestead, also known as Elmwood, is a historic house museum that documents the life of home of the American lawyer and politician Oliver Ellsworth. Built in 1781 and named after the 13 elm trees Ellsworth planted in honor of the thirteen colonies, the house boasts a wooden frame structure with a clapboarded exterior and side gable roof with end chimneys. The interiors of the house feature furnishings and decorative materials typical of the late 19th century and tours of the house can be arranged on request. Owned and maintained and operated as a museum by the Connecticut Daughters of the American Revolution, the house is listed on the National Register of Historic Places and is a National Historic Landmark.

778 Palisado Ave, Windsor, CT 06095, Phone: 860-688-8717

Where to Eat

7. Bear's Smokehouse BBQ


"Savor smoky brisket and enjoy casual eats on an easy lunch stop."

Bear's Smokehouse BBQ

© Bear's Smokehouse BBQ

Bear's Smokehouse BBQ is a local BBQ chain that serves hickory-smoked meats, along with hearty sandwiches, fresh salads, and sides in a casual, low-key setting. Beginning as a takeout counter, the locally owned and operated business grew into a favorite go-to spot for deliciously smoked barbecue meats, classic sides, and housemade sauces. Prepared from family recipes and made with fresh, locally sourced ingredients, including grass-fed, prime beef, pork, and chicken, Bear's Smokehouse BBQ can be enjoyed in one of the many restaurant chains around the state, one of the food trucks or a concessions takeout, or at one of the restaurant’s award-winning catered events. Bear's Smokehouse BBQ is open for lunch and dinner, seven days a week.

2152 Poquonock Ave, Windsor, CT 06095, Phone: 860-785-8772

8. Union Street Tavern


Among my top 10: "Relax with pub fare and craft beer during a cozy weekend meal."

Union Street Tavern

© Union Street Tavern

The Union Street Tavern is a casual neighborhood gathering spot set in an old brick firehouse that serves a creative menu of with innovative American pub grub. Blending classic tavern-style dining with an element of elegance, the Union Street Tavern presents a menu of signature appetizers, steak, pasta, and fresh seafood dishes, all of which are prepared with fresh, locally sourced ingredients and served in a casual and relaxed atmosphere. Specialty burgers included The Imposter which is packed with a pure plant-based burger patty topped cheddar cheese, sautéed mushrooms and onions and served on a country roll, and the Trattoria Burger with roasted bell peppers, pesto mayonnaise and smoked mozzarella. The Union Street Tavern is open for lunch and dinner, seven days a week.

20 Union St, Windsor, CT 06095, Phone: 860-683-2899

If you are interested in local events:

  • Shad Derby Festival (May) – Windsor’s signature celebration with parades, fishing tournaments, craft fairs, and community fun.
  • Summer Concerts on the Green (June–August) – Weekly music series held in the heart of downtown.
  • Farmers’ Market at the Library (Summer) – Local produce, baked goods, and crafts available weekly through the season.

If you are looking for unique day trips within 30–60 Minutes of Windsor, CT:

  • Hartford (15–20 min) – Visit the Mark Twain House, Connecticut Science Center, and Bushnell Park.
  • Springfield, MA (25–30 min) – Explore the Basketball Hall of Fame and Dr. Seuss Museum in this family-friendly city.
  • Old Wethersfield (20 min) – Stroll Connecticut’s oldest historic district filled with colonial homes and charming shops.
  • Collinsville (35–40 min) – Browse art studios, kayak the Farmington River, or bike the Farmington Canal Trail.
  • New Haven (50–60 min) – Explore Yale University, top-notch museums, and pizza famous worldwide.

I get asked this a lot so I decided to include it:

  • Where is Windsor located?
    • Resting on the northern border of Connecticut's capital, Hartford, in Hartford County, Windsor was the first English settlement in the state.
  • What outdoor attractions can visitors explore in Windsor?
    • Notable attractions in this quaint town include Northwest Park, a Nature Preserve that offers:
      • Hiking and walking trails
      • A nature center
      • Soccer fields
  • What cultural experiences does Windsor offer?
    • The Windsor Art Center provides opportunities for visitors to enjoy a variety of theatrical and arts-related programs.

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