If you're craving small-town charm with colonial history, I think you’ll love Windsor. When I first visited Connecticut’s oldest town, I didn’t expect to find such a rich blend of riverside recreation, local dining, and quiet New England beauty. I’ve spent afternoons exploring museums, paddling down the Farmington River, and just soaking in the cozy vibe along Main Street. If you're anything like me, you'll find Windsor to be peaceful—but far from boring.

Windsor, CT Highlights:

  • For Families: Visit Northwest Park – I always recommend this spot when you’ve got kids or just want fresh air. With its 473 acres of walking trails, farm animals, and a nature center, you’ll find it’s a perfect place to slow down and enjoy a picnic.
  • For Outdoor Enthusiasts: Paddle the Farmington River – I’ve kayaked this stretch myself, and it’s so calm and scenic. If you’re up for a relaxing outdoor adventure, you should definitely get on the water.
  • For Kids: Play at Windsor Meadows State Park – I’ve brought my niece here, and she had a blast. If you’re traveling with little ones, you’ll appreciate the open space, river views, and family-friendly paths for biking or walking.
  • For an Adventure: Bike the Windsor River Trail – I discovered this trail by chance, and now I always recommend it. It’s a quiet, flat path with beautiful river views—great if you want to jog, walk, or cycle in peace.
  • For Shoppers: Explore downtown Windsor – I love strolling the historic Main Street corridor. You can pop into charming boutiques, sip coffee at a local café, and admire the colonial architecture while you’re at it.

Best Time to Visit Windsor, CT

I’ve found the sweetest time to visit Windsor is from May to October. If you’re like me and enjoy warmer weather and blooming scenery, spring and summer are ideal. Fall, though—that’s when Windsor really shines. You’ll get those crisp mornings and fiery foliage that make New England so magical.

How to Get to Windsor, CT

  • By Car: I usually drive in from Hartford—it’s just a 15-minute trip up I-91. If you’re coming from Springfield, MA, you’ll be there in half an hour.
  • By Train: I’ve used Amtrak and CTrail’s Hartford Line before—super easy if you're coming from places like New Haven or Springfield. You can sit back, relax, and skip the traffic.
  • By Air: Whenever I fly into Bradley International (BDL), I’m always surprised how close Windsor is—just 10 minutes away. If you’re flying in, you’ll be settled in no time.

Where to Stay in Windsor, CT

  • Hilton Garden Inn Hartford North/Bradley Int’l Airport – I’ve stayed here after a late flight—it’s super convenient, with comfy rooms and a shuttle service that makes life easy.
  • Marriott Hartford/Windsor Airport – I like this one for a weekend stay. You’ll have space to spread out, a pool to unwind in, and quick access to I-91.
  • Residence Inn by Marriott – If you’re staying longer, I think you’ll appreciate the suites and kitchenettes. It’s quiet, suburban, and feels like home.

Best Things to Do in Windsor, CT

Northwest Park

Thomas/stock.adobe.com

Northwest Park - Hike peaceful trails and visit farm animals on a relaxing family trip.                                    

Vintage Radio and Communications Museum of Connecticut

Vintage Radio and Communications Museum of Connecticut

Vintage Radio and Communications Museum of Connecticut - Explore old tech and discover unusual gadgets in this affordable museum stop.                                    

Keney Park Golf Course

Keney Park Golf Course

Keney Park Golf Course - Play scenic fairways and enjoy a quiet weekend round near the city.                                    

Windsor Historical Society

Windsor Historical Society

Windsor Historical Society - Tour colonial homes and learn local stories on this quick educational outing.                                    

Windsor Arts Center

Windsor Arts Center

Windsor Arts Center - Admire local exhibits and catch live performances in a charming cultural attraction.                                    

Oliver Ellsworth Homestead

Oliver Ellsworth Homestead

Oliver Ellsworth Homestead - Step into history and explore this preserved home on a quiet retirement visit.                                    

Bear's Smokehouse BBQ

Bear's Smokehouse BBQ

Bear's Smokehouse BBQ - Savor smoky brisket and enjoy casual eats on an easy lunch stop.                                    

Union Street Tavern

Union Street Tavern

Union Street Tavern - Relax with pub fare and craft beer during a cozy weekend meal.                                    

If you are interested in local events:

  • Shad Derby Festival (May) – If you’re in Windsor in May, don’t miss the Shad Derby Festival. It’s the town’s signature event, with parades, fishing tournaments, and tons of fun. I always have a great time soaking in the community spirit here!
  • Summer Concerts on the Green (June–August) – From June to August, enjoy the weekly music series in downtown. I love heading over with friends to relax on the grass while enjoying live music. It’s the perfect way to unwind on a summer evening.
  • Farmers’ Market at the Library (Summer) – You’ve got to check out the Farmers' Market at the Library during summer. You’ll find fresh local produce, baked goods, and crafts – all the essentials for a great market day. It’s a favorite of mine for picking up treats and supporting local vendors.

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

  • Hartford (15–20 min) – Hartford is so close, and there’s so much to see! You can visit the Mark Twain House, the Connecticut Science Center, or enjoy a stroll in Bushnell Park. It’s a perfect place to explore for a day.
  • Springfield, MA (25–30 min) – If you’re up for a short drive, Springfield has some great family-friendly attractions like the Basketball Hall of Fame and the Dr. Seuss Museum. It’s a fun way to spend the day, especially with kids!
  • Old Wethersfield (20 min) – If you’re in the mood for some history, Old Wethersfield is the place to go. It’s Connecticut’s oldest historic district, filled with colonial homes and charming shops. It’s one of my favorite spots for a leisurely afternoon walk.
  • Collinsville (35–40 min) – Collinsville is great for art lovers and outdoor enthusiasts alike. You can browse art studios, kayak the Farmington River, or bike the Farmington Canal Trail. I love how active and creative the vibe is in this area!
  • New Haven (50–60 min) – If you feel like a bit of a drive, New Haven has a ton to offer. You can visit Yale University, explore top museums, and of course, try some of the world’s best pizza. It’s a must-see if you’re in the area!

Frequently Asked Questions:

  • Where is Windsor located?
    • Windsor is nestled on the northern border of Hartford, Connecticut’s capital. It’s actually the first English settlement in the state, so you’re stepping into a bit of history when you visit.
  • What outdoor attractions can visitors explore in Windsor?
    • If you love the outdoors, Windsor has some great spots to explore, like Northwest Park. It’s a lovely nature preserve with:
      • Hiking and walking trails that I think you’ll enjoy
      • A really informative nature center
      • And even some soccer fields if you’re into sports
  • What cultural experiences does Windsor offer?
    • The Windsor Art Center is a wonderful place if you’re into arts and culture. It offers a variety of theatrical performances and art programs that I’ve always found inspiring.

In Summary...

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