Things To Do In Middletown CT: Top 23 Most Unique Spots | Stanton House Inn

The waterfront along the Connecticut River near downtown Middletown, Connecticut

Middletown, Connecticut, is comfortably nestled along the Connecticut River. Its rich history dates back to 1650. That said, it’s modern cosmopolitanism is a draw in and of itself. The city’s heart is Main Street, a busy hub of restaurants, bars, and coffee shops. The downtown area boasts architecture from as far back as the 19th century. There’s also Wesleyan University, a sprawling campus centered on an 1830s mansion. The city is home to a craft brewery and a winery, each with unique stories. Middletown possesses a quintessential New England charm. And what began as a sailing port has since transformed into a great place to live, study, and visit.


Ready to explore the best things to do in Middletown? Let’s get into it:


Quick hits

  • Explore Middletown, CT’s rich history and vibrant attractions like Wesleyan University and Harbor Park.
  • Delight in outdoor activities at Wadsworth Falls State Park or Seven Falls Park. Also, experience unique events such as a beer tasting at Stubborn Beauty Brewing Co.
  • Visit nearby towns for even more fun – Middlefield, Meriden, East Hampton & Madison!

things to do in middletown ct map Things to do in Middletown CT: Top 23 Most Unique Spots
Map design by Stanton House Inn

A Brief History of Middletown, Connecticut

Main St around 1910, from the City Hall

Middletown sits proudly in Middlesex County, Connecticut. The Mattabesett Native Americans were first to call it home. The Mattabesett were part of the Algongquian-speaking tribes in the Connecticut Valley. Their leader was a single chief known as Sowheag.


English settlers arrived in 1650, giving the town its original name, Mattabeseck.


Colonial Era

In 1651, Connecticut’s General Court established a town named “Mattabesett”. Two years later, the town renamed itself Middletown. Main Street is located halfway between Windsor, CT, and Old Saybrook, Connecticut, on the Great River, after all. It appears they wanted to keep with the tradition of New England towns of naming them after hometowns or something matter-of-fact.


The Pequot Mohegan, allies of the English colonists, arrived in the area in the latter half of the 17th century. This arrival led to conflicts with the Mattabesett and other local tribes.


By the 18th century, Middletown had become the most prosperous settlement in Connecticut. One-third of its residents were involved in merchant and maritime activities. And yet, it was also a place where enslaved Africans were held as workers. By 1756, Middletown had the third-largest African slave population in the state.


Merchant traders of the time had ambitious plans. They advocated for the clearance of the Saybrook Bar at the mouth of the Connecticut River. They also sought the creation of Middlesex County in 1785. The name ‘Middlesex’ was chosen with the vision of making Middletown the head of a long river port. The long river port on the Thames in Middlesex County, England, inspired the vision.


19th Century

Berkeley Divinity School, between 1900 and 1910

Following the Revolution, Connecticut decided to abolish slavery. This decision led to the port’s decline in the early years of the 19th century. The War of 1812 brought trade restrictions. Middletown emerged as a major center for firearms manufacturing, supplying most of the pistols to the US government during the war. Wesleyan College was established in 1831 and quickly became a leading liberal arts university in the country.


In 1841, Middletown established the state’s first public high school. It welcomed all students between the ages of nine and sixteen. In the mid-19th century, manufacturing replaced trade as the city’s economic backbone.


Middletown’s residents also played an active role during the Civil War. Union General Joseph K. Mansfield and Brigadier General George Taylor were among the casualties. Some townsfolk actively participated in the abolitionism movement. The city was a hub along the Underground Railroad.


By the latter part of the 19th century, manufacturing drove the city’s economy. That said, railroad operators bypassed the city while constructing a railway between Hartford, CT, and New Haven, Connecticut. While it did limit industrial growth, the city’s pride was in its production of:

  • Metal parts
  • Machine tool manufacturers
  • Die manufacturers
  • Pioneer automobile manufacturers


Middletown even briefly hosted a major-league baseball team, the Middletown Mansfields.


20th Century

Broad Street at Washington in Middletown, around 1910

In the late 19th and early 20th centuries, Middletown was already a diverse place, with settlers from:


  • The British Isles
  • Italy
  • Poland
  • And Germany


At the same time, the local African American population dwindled down to only 53. That said, the Great Migration reversed that trend. African Americans arrived in droves seeking industrial jobs and improved living conditions.


The 1980s saw an influx of Cambodian refugees, brought to Middletown by Wesleyan professors. This marked the beginning of a thriving Cambodian community. Hindu immigrants from India and Southeast Asia also made Middletown their home. They established the first Hindu temple in Connecticut here.


The mid-20th century was a challenging period. Middletown saw a decline in heavy industry and manufacturing jobs, which led to a decrease in population. Slapping a highway between downtown Middletown and the river didn’t help, either.


The 1990s marked a significant partnership between:


  • The city of Middletown
  • The Middlesex Chamber of Commerce
  • And Wesleyan University


They made major investments in Middletown’s Main Street. The work improved its urban design and encouraged new businesses.


Today, that investment has paid off. Middletown is a busy little city that remembers its roots while offering a multicultural feel unique to this area of the state.


The Best Things to do in Middletown CT

Downtown Middletown

Middletown boasts a rich history and a variety of attractions. You can explore the downtown area and visit Wesleyan University. Or discover historical sites and museums and enjoy parks and outdoor spaces. The city also hosts local breweries and engaging adventure sports. Middletown is an adventure of a CT day trip, waiting to be explored.


Downtown Middletown

Downtown Middletown, with over 200 businesses, is the heartbeat of the city. It combines the charm of historic storefronts with the vibrancy of diverse dining options and a movie theater. Plus, it hosts a farmers’ market every Friday during summer and early fall.


The area also features Wesleyan’s High Street and Harbor Park along the bank of the Connecticut River. Why not enjoy a leisurely stroll down Main Street and see what sparks your interest?


Wesleyan University

Wesleyan University campus

Wesleyan University is a landmark in Middletown. Set in a picturesque campus of 316 acres, this liberal arts university offers an insight into the world of academia and beyond.


Take one of the guided tours of historic buildings, and peek into the Davison Art Center’s collection of 25,000 pieces. Wesleyan University is where history, art, and education converge.


Van Vleck Observatory

Van Vleck Observatory

Do you have a penchant for stargazing? The Van Vleck Observatory at Wesleyan University is an absolute must-visit. It’s one of the oldest observatories in the United States and a great source of astronomical knowledge.


It offers public observation nights each week. It’s a sweet opportunity to view celestial bodies through their three telescopes.


You can also participate in Q&A sessions to learn more about astronomy.


Harbor Park

Harbor Park waterfront

Seeking a tranquil oasis close to the city? Head to Harbor Park. Situated on the west bank of the Connecticut River, it offers:


  • Stunning waterfront views
  • Sculptures to admire
  • A perfect spot to watch the sunrise
  • A calm and peaceful atmosphere


Just remember to check the water levels as the park can potentially be submerged in the springtime. And while there is a busy thoroughfare between Main Street and the water, there are some underpasses for walkers.


General Mansfield House

If you’re a history buff, the General Mansfield House is a must-visit. Serving as the headquarters for the Middlesex County Historical Society, the house offers a glimpse into the past. Explore the formal herb garden, the border of lilacs in the spring, and the Rose Garden behind the house.


Kidcity Children’s Museum

Kidcity Children’s Museum is a paradise for kids aged 1-7. With three floors of interactive exhibits, it offers an environment where kids can explore, play, and learn.


The unique handmade exhibits include the Middleshire exhibit designed like a tiny medieval village.


Wadsworth Falls State Park

Wadsworth Falls State Park

For those drawn to the outdoors, Wadsworth Falls State Park is an ideal retreat. It offers hiking and biking trails, as well as a picnic area. The park’s centerpiece is the stunning Big Falls waterfall. This top pick among the best CT state parks, adjacent to Long Hill Estate, sprawls across 267 acres.


The jewel of the park, Wadsworth Falls, is nestled on the southwestern side. The falls owe their existence to the tumbling waters of the Coginchaug River. As it flows into the Mattabesset River’s tidal marsh, this river is an ideal route for canoeing.


Seven Falls Park

Seven Falls Park is another gem of state parks for nature lovers. A rugged, remote park with a picturesque waterfall, it offers marked trails for short to medium hikes.


Plus, one of its seven waterfalls stands tall at 181 feet. It’s an impressive sight.


Higby Mountain

Higby Mountain makes the western limit of Middletown. This 892-foot basalt mountain ridge is a part of the larger Metacomet Ridge. This ridge stretches from Connecticut into Massachusetts for a good 100 miles.


The mountain ridge extends for two miles, forming a west-facing ledge. From this vantage point, you get striking views over the neighboring city of Meriden, CT, and the Hanging Hills in the distance.


The southern trailhead of the mountain is easily accessible. Just a few minutes’ drive from downtown Middletown and a brief climb will bring you there. The unique landscape you’ll find here is due to the fault’s alkaline soils, a rarity in a state that is mostly acidic.


Wadsworth Mansion

Front elevation of the Wadsworth Mansion

The Wadsworth Mansion, a historical gem in Middletown, was built in the early 1900s. It was the New England summer getaway home of a local businessman and philanthropist, Colonel Clarence S. Wadsworth. In 1999, the mansion was restored to its former glory. Now, the Wadsworth Mansion stands on 500 acres of land, adorned with nature trails and occasional open-air markets.


This is also the current location of Daffodils on the Estate. You’re sure to have a fun time at one of the best spring festivals in CT.


Breweries in Middletown, CT

Enjoying a pint (measured in imperial units) at a Middletown brewery

Middletown, CT, is a paradise for craft beer lovers. Each brewery in town offers its unique flavor, crafting some of the finest beers you’ll ever taste. Are you a fan of hoppy IPAs, smooth stouts, or crisp lagers? You’ll find some of the best breweries in Connecticut right here in Middletown. So, grab a stool, lift a glass, and here’s to the good life in Middletown, CT.


Stubborn Beauty Brewing Company

If you’re a connoisseur of beer, Stubborn Beauty Brewing Company is worth a visit. This craft brewery offers a variety of eclectic brews and hard ciders in their tasting room for tasting and growler refills. With unique brews like Conqueror (Brown Ale), Happy Treez IPA, and How Rye I Am (Saison), it’s a paradise for beer lovers.


Forest City Brewing

Forest City Brewing is another must-visit for beer aficionados. Offering unique craft beers and a welcoming atmosphere, it’s a great spot to unwind and enjoy some quality brews. Don’t miss out on their tree-trimming party and special beers like Shinny, a spiced Belgian quad.


Bergen House

Talon and Emilie Bergen are the proud owners of this Middletown meadery. Which is fun to say.


They embarked on their brewing journey in 2011. Along the way, they made a fascinating discovery – mead doesn’t always have to be sweet, it can be dry. Their inaugural creation was an apple mead. It was potent, boasting a 20% alcohol content, and drinking it was akin to consuming liquid fire. Despite its fiery nature, it garnered a following over time.


That said, the Bergen House yearned for improvement. In pursuit of this, they established a meadery in 2017. Here, they committed to producing a new batch every week. Through relentless experimentation, they refined their product. The result? A mead with an alcohol content of 5-11%, a sparkling texture, and a refreshing taste.


Eli Cannons Tap Room

Eli Cannons Tap Room is a popular bar in Middletown that offers:


  • A wide selection of craft beers
  • A lively atmosphere
  • Rustic decor
  • Friendly staff
  • A buzzing crowd


It’s the perfect place to unwind after a day of exploring Middletown.


The Buttonwood Tree

The Buttonwood Tree is a performing arts venue and community hub. The space offers:


  • Workshops
  • Live music
  • Dance performances
  • Talks
  • Poetry readings
  • Art exhibitions


Whether you’re a devotee of the arts or simply seeking engaging entertainment, the Buttonwood Tree has got you covered.


Brownstone Adventure Sports Park

zip lining at Empower Leadership Sports & Adventure Center

Back in the late 1800s and early 1900s, Portland was quite the hot spot for brownstone. This go-to building material found its way into:

  • Manhattan’s skyscrapers

  • And graced places like Wesleyan University in Middletown

Wesleyan actually owned the quarries for a good 50 years during the 1800s. That said, flooding in the 1930s put a stop to all the digging, and the quarries were shut down.

Fast forward through years of neglect.

In 1999, Portland snapped up the old quarries right off Main Street, alongside the Connecticut River. The town bagged 2,000 feet of riverfront for a cool $1,050,000.

After some head-scratching and planning studies, the site got its badge as a National Historic Landmark. It was then that the Hayes brothers—Ed, Frank, and Sean—pitched a brilliant idea to the town. They envisioned a sports park right there in the old quarries. The town loved the idea, and gave it the thumbs up at a town meeting. And in 2006, Portland struck a 25-year deal with Brownstone Exploration & Discovery Park to turn the land into an adventure park. And just like that, history turned into high-flying fun!

For adrenaline-pumping outdoor activities, Brownstone Adventure Sports Park offers:

  • Zip lines
  • Rope swings
  • Cliff-jumping
  • Wakeboarding
  • An inflatable water park

This adventure center promises an unforgettable adventure.


Shopping in Middletown, Connecticut

Middletown offers a variety of shopping options for everyone. From local boutiques to specialty stores, you’ll find a wide range of products to choose from.


Amato’s Toy and Hobby store, in particular, is a favorite among locals and visitors alike. This family-run store offers an extensive collection of toys and hobby items.


Restaurants in Middletown, CT

Delicious Tuscan-American fusion cuisine at Luce Restaurant in Middletown, CT

Culinary enthusiasts, grab your forks! Middletown is home to an array of dining options to suit every palate.


Luce Restaurant

Luce Restaurant serves delectable Tuscan-American fusion cuisine. It has long been wowing diners with dishes like:


  • Beef carpaccio
  • Scallops
  • Maryland crab cake
  • Chicken sausage with caramelized onions
  • Seafood and veal combo


Taino Smokehouse

For barbecue aficionados, Taino Smokehouse is the place to be. Using simple ingredients – fire, pepper, and salt – they create delicious barbecue that will make you come back for more.


Don’t miss out on their mouthwatering smoked Reuben sandwich and succulent brisket.


Directions to Middletown, CT, from Greenwich, CT

Reaching Middletown from Greenwich, CT, is a breeze, whether you choose to drive, take a train, or hop on a bus. Depending on your choice of transportation, this road trip in CT takes approximately an hour and a half from our Connecticut bed and breakfast inn. And you’ll hit plenty of great places along the way, including New Haven, Connecticut.


Hotels, Inns, and Places to Stay in Middletown, Connecticut

Charming interior of the Inn at Middletown, a historic inn in Connecticut

Or stick around for an overnight stay. There’s plenty to do here and nearby to warrant a longer visit.


Inn at Middletown

The Inn at Middletown, a historic inn, goes beyond being just a place to stay; it embodies a part of Middletown’s history. With a blend of historic charm and modern amenities, the Inn at Middletown offers a unique experience for its guests. Its exceptional customer service and attention to detail make it a top choice for accommodation in Middletown.


More Towns and Cities to Explore Near Middletown, Connecticut

sunflower field at Lyman Orchards in Middlefield, CT

If you have some extra time, why not explore the neighboring towns and cities located along the Connecticut River Valley and Connecticut coastline? Each of these locations offers its own set of unique attractions and experiences in Connecticut.


Hartford, CT

Only a 20-minute drive away from Middletown, CT, is the capital city of Connecticut. The best things to do in Hartford, Connecticut, include major museums like the Wadsworth Atheneum, as well as Bushnell Park.


Meriden, Connecticut

Lake in Meriden, CT

Meriden, also referred to as the ‘Silver City’, has a rich history as a manufacturing hub. The city of Meriden, CT, hosts several fun attractions including Hubbard Park, Meriden Green, and the Meriden Linear Trail.


East Hampton, CT

East Hampton, CT, offers a delightful mix of history and outdoor adventure. Explore the Air Line State Park Trail, visit Salmon River State Forest, or check out the Comstock Covered Bridge for an unforgettable outdoor experience.


Madison, Connecticut

shoreline of Madison, CT

Madison boasts a rich history and a charming community. The town is home to the Hammonasset Beach State Park, the Meigs Point Nature Center, and the Shoreline Greenway Trail. And that barely scratches the surface of the list of things to do and see in Madison, CT.



Middletown is a destination that offers a myriad of experiences. From exploring historical sites to partaking in outdoor activities, enjoying delectable food, and shopping for unique items, there’s something for everyone. Whether you’re considering a quick getaway or planning a week-long vacation, Middletown promises a memorable time.


Frequently Asked Questions


What is Middletown CT known for?

Middletown, Connecticut, is renowned for its rich 370-year history. It is home to the world-renowned Wesleyan University and was the former county seat of Middlesex County. The city boasts a vibrant downtown Main Street, which is a hub of international restaurants, shops, and entertainment.


Does Middletown CT have a downtown?

Indeed, Middletown, CT, boasts a bustling downtown area. This area is filled with a variety of restaurants, cafes, shops, and businesses. Downtown Middletown is undergoing a Renaissance, with each of its many sub-districts displaying a unique character.


Is Middletown CT a nice place to live?

Middletown, a suburban town densely populated with a variety of activities, restaurants, and parks, caters to residents of all ages. Its central location in Connecticut places it conveniently close to major cities and attractions, making it an ideal setting for family living. In summary, Middletown presents itself as a fantastic living option.


What is the nickname for Middletown CT?

Middletown carries the nickname “Forest City.” This moniker dates back to the 1800s, thanks to the city’s tree-lined streets.


What are the top attractions in Middletown, CT?

Middletown, CT, is home to a variety of top attractions. These include the delightful Downtown Middletown and the prestigious Wesleyan University. For astronomy enthusiasts, the Van Vleck Observatory is a must-visit. Those seeking tranquility can visit Harbor Park, while families with children can enjoy the Kidcity Children’s Museum. Nature lovers will appreciate the Wadsworth Falls State Park and Seven Falls Park. History buffs can explore the Wadsworth Mansion. Beer aficionados can sample local brews at Stubborn Beauty Brewing Company, Forest City Brewing, and Bergen House. The Eli Cannons Tap Room is a popular spot for unwinding. The Buttonwood Tree offers cultural experiences, and thrill-seekers can head to the Brownstone Adventure Sports Park.



  1. It would be nice if you mentioned that the Brownstone Adventure Park is located in Portland. It would also be nice if you described the history of the quarries.

  2. Thanks for the recommendations! I agree that I wasn’t clear as to where Brownstone Adventure Park is located. I just updated the location for Brownstone Adventure Park.

    I have to admit, I didn’t stumble upon any mention of quarries when I was researching the history of Middletown. But with a little extra digging, I found some, thanks to your encouragement! The history section is always my favorite part to write.

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