Middlebury, Connecticut is a hidden gem waiting to be discovered. This charming New England town offers a perfect blend of history, natural beauty, and small-town charm.
You’ll find plenty to see and do in Middlebury.
From exploring scenic hiking trails to visiting local farms and orchards.
Nestled in the heart of Connecticut, Middlebury boasts a rich history dating back to the 18th century.
You can stroll through the quaint downtown area, admiring well-preserved historic buildings and browsing unique local shops.
Nature lovers will appreciate the town’s many parks and green spaces. Perfect for picnics or peaceful walks.
Whether you’re seeking a relaxing weekend getaway or a family-friendly vacation spot, Middlebury has something for everyone.
With its convenient location and welcoming atmosphere, this delightful Connecticut town is sure to leave a lasting impression on visitors of all ages.
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How To Get To Middlebury
Getting to Middlebury, Connecticut is easy and convenient. You have several options for travel, depending on your starting point and preferences.
If you’re driving, Middlebury is accessible via major highways. Take Interstate 84 and exit onto Route 64 or Route 188.
The town is about a 2-hour drive from New York City and 3 hours from Boston.
Train travel is another option.
The nearest Amtrak station is in Waterbury, just a short drive from Middlebury. From there, you can take a taxi or rideshare to reach your final destination.
Bus services also connect Middlebury to nearby cities. Check local schedules for the most up-to-date information on routes and times.
For those flying in, the closest major airports are:
- Bradley International Airport (BDL) in Hartford
- Tweed New Haven Airport (HVN)
- Westchester County Airport (HPN) in White Plains, NY
From these airports, you can rent a car or take a shuttle service to Middlebury.
Once in town, walking or biking is a great way to explore the charming streets and local attractions.
Taxis and rideshare services are also available for longer trips within the area.
What To See In Middlebury
Middlebury offers a mix of charming attractions for visitors. You’ll find plenty to explore in this quaint Connecticut town.
Start your visit at the St. George’s Episcopal Church. This historic site showcases beautiful architecture and provides a peaceful spot for reflection.
Art lovers should head to the Town Hall Theater. This restored landmark hosts a variety of performances, from musicals to plays. You might catch a local production or a simulcast from the Metropolitan Opera.
For outdoor fun, visit Quassy Amusement & Water Park. This family-friendly attraction offers thrilling rides, water slides, and a beach on Lake Quassapaug. It’s perfect for cooling off on hot summer days.
Nature enthusiasts will enjoy the Middlebury Land Trust trails. These scenic paths wind through forests and fields, providing great opportunities for hiking and birdwatching.
Don’t miss the Middlebury Historical Society Museum. Here, you can learn about the town’s rich history through exhibits and artifacts.
Finish your day with a stroll through Meadowview Park. This green space features walking paths, picnic areas, and beautiful views of the surrounding landscape.
Where to Stay in Middlebury
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 Middlebury
Middlebury, Connecticut has a rich past dating back to the 18th century. The town was incorporated in 1807 from parts of Southbury, Waterbury, and Woodbury. Its name comes from its location in the middle of these communities.
In the early days, Middlebury’s economy was based on agriculture. Small industries like blacksmithing supported farming activities. As you explore the town, you’ll see remnants of this rural heritage.
The 19th century brought changes to Middlebury. Textile mills appeared, diversifying the local economy. These mills played a key role in the town’s growth and development.
Education has long been important in Middlebury. The former Middlebury Central School, built in 1898, stands as a testament to this commitment.
For history buffs, the Middlebury Historical Society is a must-visit. Founded in 1945, it preserves and shares the town’s history through various exhibits and programs.
As you wander Middlebury’s streets, you’ll feel a connection to its past. The town’s careful preservation of historic buildings and sites allows you to step back in time and experience Connecticut’s rich heritage firsthand.
Towns Near Middlebury
Middlebury, Connecticut is surrounded by several charming towns and cities worth exploring. You’ll find a mix of urban and rural environments within a short drive.
Waterbury, just 6 miles east, offers urban attractions and historical sites. It’s known for its brass industry history and vibrant downtown area.
Southbury, bordering Middlebury to the southwest, boasts scenic landscapes and outdoor recreation. You can enjoy hiking trails and picturesque views of the Housatonic River.
Woodbury, famous for its antique shops, lies about 7 miles northwest. It’s a perfect spot for collectors and history buffs.
Naugatuck, 8 miles southeast, features beautiful parks and nature preserves. You’ll love exploring its green spaces and walking trails.
Oxford, located 7 miles south, offers a quiet, rural atmosphere. It’s ideal for those seeking a peaceful retreat from bustling city life.
Watertown, about 5 miles north, combines small-town charm with modern amenities. You’ll find local shops, restaurants, and community events here.
These nearby towns provide diverse experiences, from urban exploration to natural getaways. Each offers unique attractions, making the area around Middlebury an exciting destination for travelers.
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