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 and traced by restaurants, bars and coffee shops.
Downtown Middletown is endowed with genteel architecture from the 19th-century, and 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, while the old forests, mountain ridges and waterfalls of rural Middletown are 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), who 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 attraction at the park are of course, the two waterfalls, both easily accessed by trails: Wadsworth Big Falls drops more than nine metres from a shelf of Hampden basalt, and Wadsworth Little Falls, on the brook of the same name, slips down shelves on a sandstone outcrop from a height of 12 metres.
The park also has a pond and sandy beach for swimming in summer, streams for fishing and a well-kept picnic area.
2. Brownstone Exploration & Discovery Park
A day loaded with adrenaline-pumpng activities is on the cards at this flooded quarry on the east bank of the Connecticut River.
The Brownstone Exploration & Discovery Park has 11 zip lines, an inflatable water park filled with crazy obstacles, as well as a climbing wall, an “extreme” rope swing, cliff-jumping and wakeboarding.
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, and there’s a concession stand for hunger-sleighing food, snack shacks around the park and a brick oven for pizzas.
3. Kidcity Children’s Museum
For kids aged 1-7, Kidcity is three floors of experiential learning at the historic Camp-Sterns House (1835), which was lifted onto a truck and moved a couple of hundred metres 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, which 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, and Toddler Sea Caves is a space for the museum’s youngest visitors, inhabited by dancing mermaids.
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.
4. 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 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-20th century), Japanese and American artists.
Selections from this large inventory go into the gallery’s themed exhibitions, featuring the work of Jacques Callot, Lucan Cranach the Elder, Albrecht Dürer, Otto Dix and many more.
All exhibitions are accompanied by gallery talks and lectures.
5. Higby Mountain
Middletown’s western limit is walled by this 272-metre basalt mountain ridge, belonging to the larger Metacomet Ridge, which runs north to south through Connecticut and into Massachusetts for 100 miles.
The fault at Higby Mountain continues for two miles as a panoramic west-facing ledge, with striking views over the neighbouring city of Meriden and the Hanging Hills in the distance.
The southern trailhead can be reached by road within 15 minutes of downtown Middletown, and leads you into a landscape with a unique ecosystem caused by the fault’s alkaline soils in a state that is mostly acidic.
6. Stubborn Beauty Brewing
Middletown’s favourite craft brewery has been in business for over a decade and is based in an unpretentious spot at the 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.
At the time of writing in summer 2019 there was a typically eclectic range of brews on tap, like the Conqueror brown ale, Happy Treez IPA, Secret Agent (a Belgian strong ale), Sour Tiddy’s (Old Bruin), The Fist (double IPA) and My Love is Warmer than Chocolate Fudge (stout).
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 a couple of hundred metres of boardwalk decorated with sculpture, where you can linger for a while 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, and the open skies make this a handy vantage point for Middletown’s 4th of July fireworks.
In summer the Lady Katharine cruise boat, based in Essex, stops at Harbor Park on a host of themed river cruises, from a murder mystery to Gatsby’s Gala.
8. 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 making reds from Malbec, Merlot, Cab Franc, Marquette, Baco Noir and Catawba, and whites from Chardonnay, Sauvignon Blanc, Riesling, Vidal Blanc and Cayuga.
Arrigoni Winery produces some 20 award-winning wines, and Friday to Sunday you can call in for a tasting.
The Classic package ($10.95) pours five different wines, including the highly-recommended varietals Ruby (Merlot) and Rozy (Pinot Noir). There’s an indoor tasting room, and in good weather you can chill out beneath a parasol on the patio, watching the sun go down over the vineyard and enjoying some live music.
9. Mattabesett Trail
Belonging to Connecticut’s 800-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, re-entering Middletown on its west end and taking in Higby Mountain and 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 is surprisingly forgiving despite the rocky terrain.
The Mattabesett Trail has recently become part of the New England National Scenic Trail, continuing north for 233 miles to the Massachusetts-New Hampshire state line.
10. Empower Leadership Sports and Adventure Center
The ancient hardwood forest in the south of Middletown is ripe for adventure, and that’s just what awaits you at Empower.
Here you can ride hundreds of metres of zip lines and take part in all manner of tree-top experiences.
The signature experience is the two-hour Zip Line Canopy Tour, where you’ll tackle a trail more than half a mile long, through the forest canopy, riding zip lines up to 200 metres long and braving high ropes challenges like a cargo net and tight wire traverses.
There’s also a popular Map & Compass Scavenger Hunt, and on the Tree Climb Adventure you’ll scale a huge, 150-year-old oak tree and swing between two giant hickories.
You can also book special evening experiences, like Twilight Zip Line Canopy Tours at sunset, and Moonlight Zip Tours after dark between May and November.
11. McCutcheon Park
On the hilly south shore of Crystal Lake is a mostly undeveloped park, still endowed with marked hiking trails, a beach area, pavilions, grottoes, basketball courts, baseball fields, a boat launch and horseshoe pits.
The woodland at McCutcheon Park feels almost primeval, but you might be surprised to learn that a century ago this spot was much busier, and had a large outdoor stage for vaudeville acts, high-divers and even parachute jumps.
The red-blazed trail is the most scenic, leading you past mountain laurel bushes and up to a craggy overhang.
There are lifeguards on the beach in summer, and the beach is shaded by foliage.
12. 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, a Union general in the Civil War who was killed in 1862 at the Battle of Antietam.
When we put this list together in 2019 the Historical Society had a long-term exhibition lifting the lid on Middletown’s role as a port for the slave-based Caribbean sugar industry, while you could also find out about life in Middletown during World War I.
The house’s gardens are also open to the public during daylight hours, with a herb bed in front and a boxwood hedges, a rose garden and 150-year-old ginkgo tree out back.
13. Seven Falls State Park
Out in the more remote southern end of the city, the Mattabesett Trail wends its way 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.
You could have a fun time trying to jump from rock to rock, or set off on a full-on bouldering adventure of that’s your sort of thing.
There are picnic tables close to the falls, and the park is coursed with other marked trails for short to medium hikes.
14. The Buttonwood Tree
A community arts venue in Middletown’s North End, The Buttonwood Tree is a multidisciplinary space, putting on intimate art exhibitions, live music, dance performances, open mic nights, talks, poetry readings and a long list of workshops and classes, from watercolours for youth and teens to meditation, self-help and yoga.
As a community-oriented hub, The Buttonwood Tree means many things to many people, be it a place to grab coffee, a second-hand bookstore, an art gallery or performance venue.
15. Indian Hill Cemetery
If you’re wondering why a burial ground belongs on the list, Indian Hill Cemetery is one of the most scenic and peaceful places in Middletown.
It rises just west of the Wesleyan University Campus, and affords marvellous panoramas of the Connecticut River.
A consequence of the America Beautiful movement, the cemetery was established in 1850, in what was then 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, especially from the neighbouring university, soaking up the calming greenery and far-off vistas.
An enduring monument here is the brownstone neo-Gothic chapel, which grew up in the late-1860s and abounds with stained glass and daintily carved woodwork.