Top 15 Attractions and Activities in Middletown, CT

Summary

Wadsworth Falls State Park
Wesleyan University
Downtown Middletown
Kidcity Children’s Museum
Davison Art Center
Higby Mountain
Harbor Park
Brownstone Adventure Park
Mattabesett Trail
Stubborn Beauty Brewing
General Mansfield House
Seven Falls Park
Arrigoni Winery
The Buttonwood Tree
Indian Hill Cemetery

Situated on the west bank of the Connecticut River and established in 1650, Middletown is a medium-sized college city with a rich history in manufacturing and shipping.

The essence of Middletown is primarily found along the tree-lined Main Street. Just one block from the river, this thoroughfare is lined with a variety of restaurants, bars, and coffee shops.

Downtown Middletown features impressive architecture from the 19th century, which complements Wesleyan University, situated on a nearby hill and home to an art museum housed in a grand mansion dating back to the 1830s.

For culinary experiences, there is a renowned craft brewery, along with a winery located across the river. Additionally, the lush forests, mountain ridges, and waterfalls in the rural areas surrounding Middletown offer ample opportunities for outdoor activities.

Let us examine the top attractions in Middletown:

1. Wadsworth Falls State Park

In the early 20th century, this stunning tract of land, encompassing waterfalls, streams, forests, and meadows, was owned by Colonel Clarence C. Wadsworth (1871-1941). He was a member of the New York National Guard, and a notable linguist and conservationist.

His opulent residence, Wadsworth Mansion at Long Hill, stands on the Middletown side of the state park and is available for event rentals.

The main draws of the park are the two waterfalls, both accessible via trails: Wadsworth Big Falls cascades 30 feet from a shelf of Hampden basalt.

Additionally, Wadsworth Little Falls, located on the brook of the same name, descends 39 feet over sandstone outcrops.

It is without a doubt a splendid place for hiking, featuring seven different trails weaving through the woodlands. The park also includes a pond and sandy beach for summer swimming, streams for fishing, and a well-maintained picnic area.

2. Wesleyan University

Founded in 1831, this private liberal arts university boasts notable alumni such as Lin-Manuel Miranda and Bill Belichick. Located adjacent to downtown Middletown, the picturesque campus invites exploration. Guiding tours are available through the Office of Admission.

Alternatively, visitors may opt for a self-guided tour, for which the university has produced a map highlighting approximately two dozen points of interest.

The campus spans a compact 360 acres, yet offers numerous sights to admire, particularly along the majestic High Street.

Noteworthy is the stunning Russell House (1828), regarded as one of the premier Greek Revival mansions in the nation. Similarly captivating is the Alsop House (1839), now home to the Davison Art Center, which will be discussed later.

Furthermore, the Van Vleck Observatory (1914) hosts a variety of public programmes. At the time of this writing, there were Space Nights, monthly Saturday night observations, and events for children.

3. Downtown Middletown

Encircled by the Metacomet Ridge and Connecticut River, Middletown’s downtown is both beautiful and lively. Along seven walkable blocks of Main Street, approximately 200 businesses reside, many showcasing charming historic storefronts.

This vibrant atmosphere is the result of significant investment and revitalization efforts since the late 20th century, transforming Middletown into a hub for shopping, dining, socializing, and entertainment.

Downtown offers an array of culinary choices, featuring over a dozen diverse cuisines, including Italian, Hawaiian, Japanese, Peruvian, Mexican, Thai, and Cajun. Additionally, Middletown is home to a multiplex theatre located in the city center, known as Metro Movies 12.

During the summer and early fall, a farmers’ market operates on Fridays at Union Green. Just east of Main Street, the stately High Street showcases historic residences, now part of Wesleyan University. Continuing eastward leads to the scenic riverbank at Harbor Park.

4. Kidcity Children’s Museum

Targeted towards children aged 1-7, Kidcity spans three floors of interactive learning within the historic Camp-Sterns House (1835), which was relocated to its current site in 1997.

All exhibits at Kidcity are custom-designed by an in-house team, making them unique to this space. This exclusivity contributes to the attraction’s loyal following.

To provide an understanding of the offerings, at the Fishery children can engage with pulleys and conveyors to simulate fishing, while Middleshire features a miniature village designed for kids, including a castle.

One area, Toddler Sea Caves, captivates younger visitors with dancing mermaids, accessible only to children aged two or younger.

Additional attractions include a replica of a typical Main Street, a farm area, and various play items such as trains, costumes, puppets, building blocks, and dolls.

5. Davison Art Center

The Davison Art Center, established in 1952 at the elegant Alsop House built in the late 1830s, serves as Wesleyan University’s art museum. The structure itself is an artistic landmark, representing a transition between Greek Revival and Italianate styles.

The center is open from September to May and has amassed a collection of approximately 25,000 pieces over the past 70 years.

The collection includes a significant number of original prints and photography, featuring works by European (Renaissance to 20th century), Japanese, and American artists.

Exhibitions are curated from this extensive collection and focus on themes including notable artists such as Jacques Callot, Lucas Cranach the Elder, Albrecht Dürer, and Otto Dix. Each exhibition is accompanied by gallery discussions and lectures.

At the time of my last visit, the museum was temporarily closed but scheduled to reopen in the following months.

6. Higby Mountain

Middletown is bordered to the west by the prominent 892-foot basalt ridge known as Higby Mountain. This natural feature is part of the larger Metacomet Ridge, which extends north to south through Connecticut and into Massachusetts, spanning 100 miles.

This geologic fault reveals a two-mile panoramic west-facing ledge. From this vantage point, visitors can enjoy breathtaking views over the nearby city of Meriden and the scenic Hanging Hills in the distance.

The southern trailhead is easily accessible by car within minutes of downtown Middletown. After a short ascent, hikers will find themselves in an ecosystem with unique characteristics due to the alkaline soils resulting from the fault, which contrast sharply with the predominantly acidic soils of the state.

7. Harbor Park

For a tranquil experience in Middletown, one should visit the west bank of the Connecticut River.

Harbor Park features several hundred feet of boardwalk adorned with sculptures. It is a delightful spot to relax and observe the shimmering river under sunlight while gazing toward the Arrigoni Bridge’s steel arch to the north.

This park faces east, providing a stunning view of the sunrise. The expansive space also serves as an ideal vantage point for Middletown’s Fourth of July fireworks display.

It is advisable to monitor water levels, as this area may be prone to flooding during the spring.

8. Brownstone Adventure Park

For thrilling outdoor activities, Brownstone Adventure Sports Park, situated on a flooded quarry on the east bank of the Connecticut River, offers an array of adrenaline-pumping experiences.

This park features 11 zip lines, a climbing wall, an “extreme” rope swing, cliff jumping, and wakeboarding. The highlight is the floating water park, which includes various inflatable obstacles to challenge visitors.

Rental options for paddleboards and kayaks are available, ranging from half an hour to a full day. To satisfy your hunger after all the action, the park offers a concession and grilling area, along with snack shacks located throughout the premises.

9. Mattabesett Trail

The Mattabesett Trail is part of Connecticut’s extensive 825-mile Blue-Blazed trail system and stretches 50 miles in a U-shape through Middletown.

The journey begins at the Connecticut River, marking the eastern tip of the U, allowing hikers to traverse a metamorphic landscape as far south as Guilford.

Subsequently, the trail curves northward, tracing the iconic Metacomet Ridge. Upon reaching the west end, it re-enters Middletown and includes the area surrounding Higby Mountain. From there, hikers can navigate to other stunning basalt formations, ultimately reaching Lamentation Mountain, located not far in Meriden.

This segment of the trail provides almost continuous breathtaking views, and despite the rugged terrain, I found it pleasantly manageable.

The Mattabesett Trail has recently been integrated into the New England National Scenic Trail, an impressive pathway that continues north for 233 miles to the Massachusetts/New Hampshire state border.

10. Stubborn Beauty Brewing

With approximately 15 years of experience, Stubborn Beauty Brewing has established itself as Middletown’s favored craft brewery. Situated within the historic Remington Rand typewriter factory in the city’s northern industrial district, the brewery offers tastings, pints, and growler refills from Thursday through Sunday, with extended hours on Fridays and Saturdays.

The brewery is celebrated for its eclectic offerings, avoiding a strict adherence to any one beer style, which provides a refreshing contrast in a region where hoppy IPAs are predominant.

During my visit, the selection was as varied as ever, featuring options such as Conqueror (Brown Ale), Happy Treez IPA, and How Rye I Am (Saison). A notable assortment of hard ciders from the nearby Spoke + Spy Ciderworks is also available.

11. General Mansfield House

The General Mansfield House, a stunning five-bay Federal-style residence built in 1817 for Samuel and Catherine Livingston Mather, serves as the headquarters of the Middletown Historical Society.

Their daughter Louisa married Joseph K. Mansfield, a Union general during the Civil War who was killed at the Battle of Antietam in 1862 after assuming command of the XII Corps of the Army of the Potomac.

At the time this article was compiled, there was a captivating exhibition focusing on the Roman Catholic St. Sebastian Feast in Middletown, celebrated annually in May for over a century.

Currently, the house/museum is accessible on Tuesdays and Thursdays from 10:00 AM to 3:00 PM.

The gardens surrounding the house are open to the public during daylight, featuring a herb bed, boxwood hedges, a rose garden, and a 150-year-old ginkgo tree.

12. Seven Falls Park

Located at the more secluded southern edge of Middletown, the Mattabesett Trail winds through a rugged, wooded terrain near the Connecticut River.

Seven Falls State Park derives its name from a picturesque waterfall situated close to Saybrook Road. This striking cascade features seven distinct falls, framed by sizable boulders that are characteristic of the park.

Visitors can enjoy exploring by hopping from rock to rock, or for those seeking a challenge, there are opportunities for serious bouldering.

Picnic tables are conveniently placed near the falls, and the property features numerous marked trails suitable for short to medium-length hikes.

13. Arrigoni Winery

Connecticut’s wine industry, though modest, boasts a robust history dating back to 1788. In Middletown, Arrigoni Winery operates a vineyard utilizing both vinifera and ‘New World’ grape varieties.

The winery produces reds from Malbec, Merlot, Cab Franc, Marquette, Baco Noir, and Catawba, as well as whites from Chardonnay, Sauvignon Blanc, Riesling, Vidal Blanc, and Cayuga.

With around 30 award-winning selections available, tastings occur from Friday to Sunday.

The Classic tasting package features five wines, including the highly recommended Ruby (Merlot) and Rozy (Pinot Noir).

The indoor tasting room becomes a beloved gathering place, especially in pleasant weather, when visitors can unwind on the patio beneath a parasol while enjoying live music and watching the sun set over the vineyard.

14. The Buttonwood Tree

Located in the North End of Middletown, The Buttonwood Tree has been a community arts venue for over three decades, offering a multidisciplinary cultural space.

This center hosts intimate art exhibitions, live music performances, dance events, open mic nights, discussions, and poetry readings. Additionally, it provides a wide array of workshops and classes, ranging from youth watercolors to meditation, self-help, and yoga.

Functioning as a community-centric hub, The Buttonwood Tree holds a unique significance for various individuals. For me, it is a welcoming space to enjoy coffee, peruse used books, appreciate art, and experience live performances.

15. Indian Hill Cemetery

The inclusion of Indian Hill Cemetery on this list may seem unusual; however, I regard it as one of the most picturesque and serene locations in Middletown.

Situated just west of the Wesleyan University Campus, it offers stunning vistas of the Connecticut River Valley.

Established in 1850 as part of the American Beautiful movement, the cemetery was originally a rural setting on the town’s western outskirts.

Although Indian Hill remains an active cemetery, it attracts a steady stream of walkers when the gates are open. Many people from the nearby university come here to appreciate the calming green surroundings and distant views.

A notable feature is the brownstone Neogothic chapel, constructed in the late 1860s, adorned with intricate stained glass and finely crafted woodwork.

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