Windsor, Connecticut Travel Guide – History, Travel, Hotels, and More!

Windsor, Connecticut offers a charming blend of history and natural beauty. As the oldest town in the state, Windsor boasts fascinating colonial landmarks and scenic outdoor spaces.

You’ll find plenty to explore in this picturesque New England destination, from its lovely town green to expansive parks and nature preserves.

Take a stroll through the historic district to admire well-preserved 17th and 18th-century architecture. Don’t miss the chance to visit Northwest Park, a sprawling 473-acre outdoor recreation area perfect for hiking, picnicking, and wildlife viewing.

For a taste of local flavor, check out Windsor’s charming restaurants and shops clustered around the town center.

Windsor’s convenient location makes it an ideal base for exploring Connecticut. You’re just a short drive from Hartford’s attractions and the scenic Connecticut River Valley. Whether you’re seeking a relaxing getaway or an active adventure, Windsor offers something for every traveler.

Find a Place to Stay in Windsor LocksCheck accommodation availability at hotels, guesthouses and apartments in Windsor Locks. No reservation fees.
Check Availability
Windsor Connecticut
Windsor Connecticut

How To Get To Windsor

Getting to Windsor, Connecticut is easy and convenient. You have several transportation options to choose from.

By air, Bradley International Airport is your best bet. It’s just a short drive away from Windsor and serves many major airlines.

If you prefer train travel, Amtrak is a great choice. Windsor has its own Amtrak station with regular service.

The train ride from Hartford to Windsor takes only 7 minutes.

Driving to Windsor is also simple. The town is well-connected by highways. Interstate 91 runs right through Windsor, making it accessible from many directions.

Bus service is available too. Local buses connect Windsor to nearby towns and cities.

Once you’re in Windsor, getting around is a breeze. You can rent a car, use local buses, or call a taxi. Many attractions are within walking distance of each other.

Remember to check schedules and book tickets in advance, especially during peak travel seasons. This will help ensure a smooth journey to this charming Connecticut town.

What To See In Windsor

Windsor offers a blend of history and nature for visitors. Start at the Northwest Park, where you can explore hiking trails and enjoy wildlife. It’s perfect for a peaceful afternoon outdoors.

History buffs will love the Vintage Radio and Communications Museum. You’ll see old radios and learn about communication technology through the years.

For a taste of local culture, visit the Windsor Historical Society. It’s home to the Huntington House Museum, where you can step back in time and see how people lived centuries ago.

Take a stroll along the Windsor River Trail. You’ll get great views of the Connecticut River and might spot some local wildlife.

Hungry? Stop by Bart’s Drive-In for a classic American meal. It’s been a local favorite for decades.

In winter, don’t miss the ice skating rink. It’s a fun activity for all ages.

Remember to check out Windsor’s charming town center. You’ll find local shops and restaurants that give you a real feel for the community.

Where to Stay in Windsor

If you know when you are planning to go but haven’t decided on accommodation, then use the map below to get an idea of which properties are available and to compare prices during the period you wish to travel.

Enter your proposed dates and use the ‘+’ to zoom in on a location and reveal more properties. Click on the price above a property to see more information.

(Please note that this selection will also include some vacation homes, AirBnBs, and VRBOs for those who are interested in that form of accommodation!)

History of Windsor

Windsor holds a special place in Connecticut’s history as the state’s first English settlement. Founded in 1633, this charming town quickly became a vital trade hub due to its location at the meeting point of the Farmington and Connecticut Rivers.

As you explore Windsor, you’ll feel the rich history all around you. The town played a key role in shaping early American life. It was home to Oliver Ellsworth, a founding father who served as the third Chief Justice of the United States Supreme Court.

Windsor’s growth was steady over the centuries. By 2010, the population had reached 29,044. This blend of historical significance and modern development makes Windsor a fascinating place to visit.

You can dive deeper into Windsor’s past at the Windsor Historical Society. Here, you’ll find exhibits that bring the town’s evolution to life, from its colonial beginnings to today.

Don’t miss the chance to see the historic houses and landmarks that dot the town. Each tells a unique story of Windsor’s journey through time, offering you a glimpse into the lives of those who shaped this remarkable community.

Towns Near Windsor

Windsor’s central location makes it easy to explore nearby towns. Just a short drive away, you’ll find Hartford, Connecticut’s capital city.

It’s packed with history and culture.

Public transportation connects Windsor to its neighbors. The Amtrak Hartford Line runs through town, making travel a breeze.

You can hop on and visit charming spots like Berlin or Meriden.

Looking for a beach day? Madison is about 40 miles away. It’s home to beautiful shorelines and quaint shops. You’ll love the small-town feel.

Want more options? Here are some towns within 30 miles of Windsor:

Each offers unique attractions and experiences. From hiking trails to historic sites, you’ll find plenty to do.

Hartford County 2025 Deals!
Get a discount of 15% to 70% on accommodation in Hartford County! Look for deals here:

Hartford County Hotels, Apartments, B&Bs

 

Nearby Town Travel Guides

Scroll to Top