Resting on the west bank of the Connecticut River and dating back to 1650, Middletown is a mid-sized college city with a manufacturing and shipping past.
Middletown’s life is mostly concentrated on the tree-lined Main Street. One block in from the river this artery is traced by restaurants, bars and coffee shops.
Downtown Middletown is endowed with grand architecture from the 19th-century. The same goes for Wesleyan University up the hill, which has an art museum in a sprawling mansion from the 1830s.
For epicurean delights there’s a celebrated craft brewery, as well as a winery across the river. I’d allow a lot of time for the old forests, mountain ridges and waterfalls of rural Middletown, all ripe for outdoor adventure.
Let’s explore the best things to do in Middletown:
1. Wadsworth Falls State Park
In the early 20th century this beautiful parcel of land, comprising waterfalls, streams, forest and meadows, belonged to Colonel Clarence C. Wadsworth (1871-1941). He was a member of the New York National Guard, but also a linguist and conservationist.
His palatial home, Wadsworth Mansion at Long Hill, is on the Middletown side of the state park, and is rented out for events.
The main attractions at the park are of course the two waterfalls, both easily accessed by trails: Wadsworth Big Falls drops 30 feet from a shelf of Hampden basalt.
Elsewhere Wadsworth Little Falls, on the brook of the same name, slips down shelves on a sandstone outcrop from a height of 39 feet.
I don’t need to tell you, it’s all a fabulous place for a hike, with seven different trails through the woodlands. The park also has a pond and sandy beach for swimming in summer, streams for fishing and a well-kept picnic area.
2. Wesleyan University
Established in 1831 this private liberal arts university counts the likes of Lin-Manuel Miranda and Bill Belichick among its alumni. Sitting next to downtown Middletown is a picture-perfect campus that needs exploring. You can do this with a guide via the Office of Admission.
Alternatively, you can take a self-guided tour, and the university has published a map with some two-dozen highlights.
The campus is condensed into a relatively small 360 acres, but there’s much to see, especially along the regal High Street.
Here, check out the spectacular Russell House (1828)—held as one of the finest Greek Revival mansions in the country. Also lovely is the Alsop House (1839), now home to the Davison Art Center, which I’ll cover later.
Elsewhere, the Van Vleck Observatory (1914), hosts a range of public programs. When I wrote this article there were Space Nights, monthly Saturday night observations, and kids’ nights.
3. Downtown Middletown
Framed by the Metacomet Ridge and Connecticut River, Middletown has a downtown area that is both scenic and vibrant. Along seven walkable blocks of Main Street there are some 200 businesses, many with elegant old storefronts.
What you see is the fruit of a lot of effort since the late 20th century, turning Middletown into a place to shop, dine, socialize, and be entertained.
There are more than a dozen cuisines available downtown, from Italian to Hawaiian, Japanese, Peruvian, Mexican, Thai and Cajun. Middletown also has a multiplex in the heart of the city, at Metro Movies 12.
In summer and early fall there’s a farmers’ market on Fridays at Union Green. Just east of Main Street is the stately High Street, lined with historic residences, now part of Wesleyan University. Go east and you’ll be on the beautiful riverbank at Harbor Park.
4. Kidcity Children’s Museum
For kids aged 1-7, Kidcity is three floors of experiential learning at the historic Camp-Sterns House (1835). This building was lifted onto a truck and moved a few hundred feet to this spot in 1997.
All of Kidcity’s exhibits are hand-built by an in-house team, and not to be found anywhere else. This is just one explanation for the attraction’s faithful following.
To give you a sense of what’s here, at the Fishery children can manipulate pulleys and conveyors to haul in a catch, while Middleshire is a kid-sized miniature village with a castle.
My youngest was transfixed by Toddler Sea Caves, inhabited by dancing mermaids. Only children aged two or younger can use this space.
There’s a reproduction of a typical Main Street and a farm, as well as all sorts of things to play with, from trains to costumes, puppets, building blocks and dolls.
5. Davison Art Center
Wesleyan University’s own art museum was founded in 1952 at the stately Alsop House, which was built in the late-1830s. The building itself is a work of art, at the transition between Greek Revival and Italianate.
The Davison Art Center is open from September to May, and over the last 70 years has gathered some 25,000 pieces.
As well as photography, much of the collection is made up of original prints, by European (Renaissance to 20th century), Japanese and American artists.
Selections from this large inventory go into the gallery’s themed exhibitions. These feature the work of Jacques Callot, Lucas Cranach the Elder, Albrecht Dürer, Otto Dix and many more. All exhibitions are accompanied by gallery talks and lectures.
When I was last in town the museum was temporarily closed and scheduled to reopen within a few months.
6. Higby Mountain
Middletown’s western limit is walled by this 892-foot basalt mountain ridge. Higby Mountain belongs to the larger Metacomet Ridge, which runs north to south through Connecticut and into Massachusetts for 100 miles.
The fault continues for two miles as a panoramic west-facing ledge. Up here I was wowed by the striking views over the neighboring city of Meriden and the Hanging Hills in the distance.
The southern trailhead can be reached by road within minutes of downtown Middletown. After a brief climb you’ll be in a landscape with a unique ecosystem caused by the fault’s alkaline soils in a state that is mostly acidic.
7. Harbor Park
For a moment of repose in Middletown the best bet is to head down to the west bank of the Connecticut River.
At Harbor Park there’s several hundred feet of boardwalk decorated with sculpture. I love to linger to watch the river twinkling in the sun, and look north to the steel arch of the Arrigoni Bridge.
The park faces east and is a fabulous spot to watch the sun come up. The open skies also make this a handy vantage point for Middletown’s 4th of July fireworks.
My word of advice is to keep an eye on the water levels, as this spot can be submerged in springtime.
8. Brownstone Adventure Park
A day loaded with adrenaline-pumping activities is on the cards at this flooded quarry on the east bank of the Connecticut River.
The Brownstone Adventure Sports Park has 11 zip lines, a climbing wall, an “extreme” rope swing, cliff-jumping, and wakeboarding. The highlight for me is the floating water park, with all kinds of inflatable obstacles to overcome.
Paddleboards and kayaks are available to rent for anything from half an hour to a full day. Naturally all this activity is going to build an appetite. The good news is there’s a concession and grilling station, as well as snack shacks dotted around the park.
9. Mattabesett Trail
Belonging to Connecticut’s 825-mile Blue-Blazed trail system, the Mattabesett Trail is a 50-mile, U-shaped path that cuts in and out of Middletown.
Starting at the Connecticut River, which marks the eastern tip of the U, you can walk a metamorphic landscape as far south as Guildford.
The trail then turns north, hugging the famous Metacomet Ridge. The trail re-enters Middletown on its west end and takes in Higby Mountain. From there you’ll traverse other spectacular basalt landforms on the way up to Lamentation Mountain not far away in Meriden.
This portion of the walk offers near-constant exhilarating scenery, and I found it surprisingly forgiving despite the rocky terrain.
The Mattabesett Trail has recently become part of the New England National Scenic Trail. This epic path continues north for 233 miles to the Massachusetts/New Hampshire state line.
10. Stubborn Beauty Brewing
Middletown’s favorite craft brewery has been in business for some 15 years. The location is the fine old Remington Rand typewriter factory in the city’s industrial north.
Stubborn Beauty Brewing opens for tastings, pours and growler refills Thursday to Sunday, with extended hours on Friday and Saturday.
The brewery has always been known for its eclecticism, never focussing on one style in particular. This can be refreshing in a region like New England, where hoppy IPAs prevail.
When I visited there was a typically varied range of brews on tap. These included Conqueror (Brown Ale), Happy Treez IPA, and How Rye I Am (Saison). There’s also a great selection of hard ciders from the neighboring Spoke + Spy Ciderworks.
11. General Mansfield House
The home of the Middletown Historical Society is a handsome five-bay Federal-style house built in 1817 for Samuel and Catherine Livingston Mather.
Their daughter Louisa married Joseph K. Mansfield, who was a Union general in the Civil War. He was killed in 1862 at the Battle of Antietam, shortly after taking command of the XII Corps of the Army of the Potomac.
When I put this list together there was a compelling exhibition about the Roman Catholic St. Sebastian Feast in Middletown. Every May, this day has been observed for more than a century in the city.
When I went to press the house/museum was open Tuesday and Thursday, 10:00 AM to 3:00 Pm.
The house’s gardens are also open to the public during daylight hours. There’s a herb bed in front and boxwood hedges, a rose garden and a 150-year-old ginkgo tree out back.
12. Seven Falls Park
Out in the more remote southern end of the city, the Mattabesett Trail loops through this rugged, wooded environment close to the Connecticut River.
Seven Falls State Park takes its name from a waterfall, set not far from Saybrook Road. This is a photo-worthy flight of seven cascading falls, flanked by the same hefty boulders that litter the park.
I had a fun time scrambling from rock to rock. If you want to get serious you can embark on a full-on bouldering adventure here.
There are picnic tables close to the falls, and the property is coursed with other marked trails for short to medium hikes.
13. Arrigoni Winery
Connecticut has a small but healthy wine industry that can trace its roots back to 1788. In Middletown there’s a vineyard and winery working with vinifera and ‘New World’ grapes.
Arrigoni Winery makes reds from Malbec, Merlot, Cab Franc, Marquette, Baco Noir and Catawba, and whites from Chardonnay, Sauvignon Blanc, Riesling, Vidal Blanc and Cayuga.
The winery produces some 30 award-winning wines, and Friday to Sunday you can call in for a tasting.
The Classic package pours five different wines, including the highly-recommended varietals Ruby (Merlot) and Rozy (Pinot Noir).
There’s an indoor tasting room, while in good weather you can chill out beneath a parasol on the patio. For me it’s a dream place to watch the sun go down over the vineyard with live music playing.
14. The Buttonwood Tree
A community arts venue in Middletown’s North End, The Buttonwood Tree is a multidisciplinary cultural space on the scene for 30+ years.
This center puts on intimate art exhibitions, live music, dance performances, open mic nights, talks, and poetry readings. There’s also a long list of workshops and classes, from watercolors for youth and teens to meditation, self-help and yoga.
As a community-oriented hub, The Buttonwood Tree means many things to many people. For me it’s a place to grab coffee, browse used books, admire art, and enjoy live performance.
15. Indian Hill Cemetery
If you’re wondering why a burial ground belongs on the list, I consider Indian Hill Cemetery among the most scenic and peaceful places in Middletown.
It rises just west of the Wesleyan University Campus, and affords marvelous panoramas of the Connecticut River Valley.
A consequence of the America Beautiful movement, the cemetery was established in 1850. In those days it was a rural location on the western outskirts of the town.
Even though Indian Hill is still active as a cemetery, when the gates are open there’s a steady flow of walkers, Many come from the neighboring university to soak up the calming greenery and far-off vistas.
An enduring monument here is the brownstone Neogothic chapel. This grew up in the late-1860s and abounds with stained glass and daintily carved woodwork.