Middletown, Connecticut offers a perfect blend of history, culture, and natural beauty.
Located on the banks of the Connecticut River, this charming city boasts a rich past and vibrant present.
You’ll find plenty to explore, from scenic hiking trails to world-class museums and delicious local cuisine.
The city’s downtown area is packed with unique shops, art galleries, and restaurants.
Wesleyan University adds a youthful energy to Middletown, with its beautiful campus and cultural events open to the public.
Nature lovers can enjoy the Mattabesett Trail, part of Connecticut’s extensive Blue-Blazed trail system, offering stunning views of the surrounding landscape.
Whether you’re interested in history, outdoor activities, or simply soaking in small-town charm, Middletown has something for everyone. Plan your visit and discover why this Connecticut gem is worth exploring.
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How to Get to Middletown
Middletown is easy to reach by various means of transportation. You have several options to get there, depending on your starting point and preferences.
By car, Middletown is accessible via major highways. It’s just off Route 9 and close to I-91.
Driving gives you flexibility to explore the area at your own pace.
If you prefer public transit, trains and buses are available. The nearest train station is in Meriden, about 15 minutes away. From there, you can take a local bus to Middletown.
For those coming from farther away, the closest airports are:
- Bradley International Airport (BDL) – about 30 minutes north
- Tweed New Haven Airport (HVN) – about 30 minutes south
From these airports, you can rent a car or use shuttle services to reach Middletown.
If you’re traveling from Manhattan, you can take a train or bus for a scenic journey through Connecticut.
Remember to check schedules and book in advance, especially during peak travel seasons.
What to See in Middletown
Middletown offers a blend of history, nature, and culture.
Start your visit at Wesleyan University, known for its stunning campus and rich academic heritage.
Take a stroll down Main Street to explore local shops and eateries. Don’t miss O’Rourke’s Diner, a town landmark serving delicious meals since 1941.
Nature lovers should head to Wadsworth Falls State Park. You can hike, picnic, and admire the beautiful waterfalls.
For family fun, visit KidCity Children’s Museum. Its interactive exhibits will delight young explorers.
Art enthusiasts will appreciate the Davison Art Center at Wesleyan University. It houses an impressive collection of prints and photographs.
End your day with a show at Oddfellows Playhouse Youth Theater. This unique venue showcases talented young performers.
For a taste of local brews, stop by Stubborn Beauty Brewing Co. Their craft beers are a hit among locals and visitors alike.
Don’t forget to enjoy the scenic views of the Connecticut River from Harbor Park. It’s a perfect spot for a relaxing evening walk.
Where to Stay in Middletown
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 Middletown
Middletown’s story begins in 1650 when English settlers founded the town. It quickly became one of the wealthiest towns in Connecticut by 1750, thanks to its thriving maritime trade.
You’ll find echoes of this rich past in the city’s well-preserved architecture.
The General Mansfield House, built in 1810, now houses the Middlesex Historical Society. It’s a must-visit for history buffs.
Middletown played a key role in the American Revolution. The town supplied ships and provisions to the Continental Army.
In the 19th century, Middletown shifted from maritime trade to manufacturing. Industries like textiles and metalworking became important.
Today, Middletown is a vibrant mix of old and new. You can explore historic landmarks while enjoying modern amenities.
The city’s diverse heritage is reflected in its neighborhoods and cultural institutions. From colonial-era buildings to contemporary art galleries, Middletown offers a unique blend of past and present.
As you walk the streets, you’ll feel the layers of history beneath your feet. Each building, each park, tells a story of Middletown’s journey through time.
Towns Near Middletown
Middletown is surrounded by charming towns that offer unique experiences for visitors to Connecticut. You’ll find a mix of coastal beauty and historic charm within a short drive.
Old Saybrook, located about 30 minutes southeast of Middletown, is a picturesque coastal town. You can stroll along the scenic Main Street, lined with quaint shops and restaurants. The town’s beaches offer relaxing spots to soak up the sun.
Essex, another gem near Middletown, is known for its well-preserved 19th-century architecture. You can take a ride on the Essex Steam Train for a nostalgic journey through the Connecticut River Valley.
Other nearby towns worth exploring include:
- Cromwell: Home to golf courses and river views
- Portland: Known for its brownstone quarries
- East Hampton: Offers lakeside recreation at Lake Pocotopaug
- Haddam: Features scenic drives and historic sites
Get a discount of 15% to 70% on accommodation in Middlesex County! Look for deals here:
Middlesex County Hotels, Apartments, B&Bs
