Top 15 Attractions and Activities in Ridgefield, CT

Overview

Keeler Tavern Museum and History Center
Weir Farm National Historic Site
Ridgefield Playhouse
Aldrich Contemporary Art Museum
Main Street
Prospector Theater
ACT of Connecticut
Lounsbury House
Devil’s Den Preserve
Pine Mountain/Hemlock Hills
Ridgefield Historical Society
Ridgefield Summerfest
Seth Low Pierrepont State Park
Hammond Museum and Japanese Stroll Garden
Saugatuck Reservoir

Situated just an hour from New York City, at the base of the Berkshires, lies a town boasting a 300-year history and an atmosphere of sophistication.

Ridgefield is distinguished by being home to the only national park in the United States dedicated to the arts, featuring the residence and studio of Impressionist artist J. Alden Weir, which stands out as one of my preferred locations in New England.

Moreover, another prominent figure in American history, architect Cass Gilbert, maintained a summer residence at the historic Keeler Tavern in Ridgefield. Presently, this site operates as a museum that merits a visit.

Main Street is lined with picturesque boutiques and restaurants, creating a vibrant atmosphere. The downtown area of Ridgefield also hosts esteemed cultural establishments, including the Aldrich Contemporary Art Museum and the Ridgefield Playhouse.

1. Keeler Tavern Museum and History Center

Rich in historical significance, the Keeler Tavern was originally constructed in 1713 and played a role in the Battle of Ridgefield in 1777. The owners during that period, Timothy and Ester Keeler, held revolutionary sympathies, which led to British troops firing upon the inn.

I was astonished to discover that a British cannonball remains lodged in a corner post after more than 240 years.

Cass Gilbert (1859-1934), the architect renowned for the Woolworth Building and the Supreme Court Building, utilized this property as a summer residence starting in 1907, making several enhancements and designing the current gardens.

The museum boasts a collection of period furnishings, art, and ceramics spanning the 18th to the 20th centuries, reflecting the evolving lifestyles of its residents.

Noteworthy artifacts in the collection include an original engraving of the Battle of Ridgefield, the initial inn sign, and family portraits. Be sure to look for the broadside of Columbus, an elephant that graced the tavern in the early 19th century.

2. Weir Farm National Historic Site

In Ridgefield, visitors can explore the residence and studio of the renowned Impressionist painter J. Alden Weir (1852-1919).

Weir referred to his estate, set within 60 acres of woodlands, fields, and waterways, as the “Great Good Place.”

This site holds great cultural significance, as it provided accommodation for numerous influential painters, including Albert Pinkham Ryder, Childe Hassam, John Twachtman, and John Singer Sargent.

From 1882 to 1919, Weir transformed the location into a summer retreat where he and his illustrious contemporaries experimented with light and color, producing timeless works of art.

Weir Farm is recognized as the only national park in America dedicated to Impressionist painting. Its charm lies significantly in the exquisite gardens and pastoral landscapes captured by Weir and his contemporaries.

Guided or self-paced tours of the Weir House, Weir Studio, and Young Studio are available.

Additionally, a comprehensive schedule of art classes is offered at this inspiring location. From May to October, visitors may also borrow free art supplies from the visitor center porch to create their own artistic endeavors.

3. Ridgefield Playhouse

This magnificent performing arts venue has been adapted from the former auditorium of Ridgefield High School.

Constructed in the late 1930s and designed by Cass Gilbert Jr., this facility was transformed into a 500-seat theater in 2000 and maintains a full calendar of events.

The programming includes a wide variety of concerts from diverse musical genres, along with comedy performances, dance displays, and film screenings. Furthermore, it features recorded productions from notable institutions, such as London’s National Theatre, as well as discussions with prominent cultural figures.

Notable names like Jim Norton, Patti LuPone, David Sedaris, Alan Ruck, and Madeleine Peyroux were scheduled during my visit.

4. Aldrich Contemporary Art Museum

Established in 1964, this esteemed independent art museum serves as a platform for innovative, emerging, or overlooked artists whose interpretations inspire creative thinking.

The Aldrich does not possess a permanent collection, instead regularly hosting inaugural exhibitions for burgeoning talent. Additionally, it showcases the work of artists in mid-career who have yet to gain widespread recognition.

The list of remarkable artists presented at the Aldrich is substantial, featuring names like Frank Stella, Cy Twombly, Robert Rauschenberg, Olafur Eliasson, Eva Hesse, and Jasper Johns.

During my visit, I was captivated by Chiffon Thomas’s ethereal, politically charged installations.

The museum’s array of programs is tailored to engage individuals of all ages with contemporary art. Look out for expert discussions, tours, and workshops.

5. Main Street

What elevates Ridgefield among Connecticut’s finest towns is its elegant main thoroughfare, replete with charming storefronts and solemn civic architecture.

A cursory glance at the painted storefronts, meticulously maintained trees, shrubs, flowerbeds, and fountains reveals the community’s commitment to maintaining Main Street’s charm.

The street is home to numerous local businesses, including bookstores, toy stores, florists, jewelry shops, lingerie boutiques, and an array of fashion and design stores.

The dining options offer a world tour within mere blocks, featuring Mexican cuisine (Baja Cocina), French bistro fare (Luc’s Café), and artisanal pizza (850 Degrees). Additionally, there are specialty shops, cafes, hotdog stands, taverns, and numerous live entertainment choices.

Directly across from the Ridgefield Library on Main Street lies Ballard Park, boasting formal gardens over five acres. This serene space is ideal for outdoor events and summer concerts, which I will discuss further.

6. Prospector Theater

There is much to admire about this state-of-the-art first-run movie theater in Ridgefield. The Prospector Theater operates as a non-profit organization established to provide employment opportunities for individuals with disabilities.

Located just off Main Street, it is surrounded by a variety of restaurants.

The theater contains four screens, including two on the main floor, one upstairs furnished with bean bags and Eames lounge chairs, and a cozy little room in the basement.

The lobby features concessions, along with a café serving beer and wine by the glass. Since its opening in 2014, the theater has showcased striking design elements both internally and externally, complemented by an exceptional sound system.

7. ACT of Connecticut

A Contemporary Theatre of Connecticut (ACT) is a newly established producing theater located at 36 Quarry Road in Ridgefield, presenting Broadway-style productions for limited runs.

During my visit, upcoming performances included Sunset Boulevard, Kinky Boots, and Million Dollar Quartet, in addition to new musicals and plays, seasonal events, and an annual gala in June.

Each production combines the expertise of Broadway professionals with local talent from Fairfield and Westchester Counties.

In addition to performances, ACT operates a conservatory program offering workshops, camps, and youth education classes.

8. Lounsbury House

This distinguished mansion, constructed in the Classical Revival style in 1895, establishes an upscale ambiance in the heart of Ridgefield. Lounsbury House was commissioned by Phineas C. Lounsbury, the 53rd Governor of Connecticut (1841-1925).

The design is originally modeled after the Connecticut State Building displayed at the 1893 Columbian Exposition in Chicago.

In 1945, the property was gifted to the town and has since functioned as a venue for both private and public events. I highly recommend attending the Music at the Mansion series, featuring exceptional chamber music performances.

9. Devil’s Den Preserve

Encompassing over 1,750 acres, Devil’s Den represents the largest Nature Conservancy preserve in Connecticut and is among the larger preserves in the Metropolitan New York Area.

The preserve features 20 miles of trails weaving through densely wooded landscapes that include wetlands, a gorge, an 18th-century millpond, streams, and high ridges offering distant vistas.

Memorable highlights include Ambler Gorge with its rugged cascades and the striking rock formation at Great Ledge.

This area sustains more than 500 species of trees and wildflowers, showcasing blooming plants such as Indian pipe, cardinal flower, and pink lady’s slipper.

Additionally, wildlife inhabitants include bobcats, red foxes, coyotes, and eastern copperhead snakes, alongside over 140 species of birds.

10. Pine Mountain/Hemlock Hills

For nature enthusiasts, there exists a collection of splendid open spaces in the northern part of Ridgefield, which together form a vast expanse of wilderness, characterized by rolling hills, fields, and scenic overlooks.

The eastern section comprises the 368-acre Pine Mountain Reserve, while the western side is designated as Hemlock Hills.

The southern boundary is defined by three large bodies of water: Lake Windwing, Rainbow Lake, and Bennett’s Pond, the latter situated within a state park.

This region encompasses some of Ridgefield’s highest elevations, traversable through a network of trails.

A red-blazed trail links Hemlock Hills with Pine Mountain, while the red and yellow blazed Ives Trail stretches from Bennett’s Pond to Hemlock Hills, passing locations pertinent to the celebrated 20th-century composer, Charles Ives.

11. Ridgefield Historical Society

Visitors can delve deeply into the rich 300-year history of Ridgefield at the Ridgefield Historical Society, located at the Scott House, which dates back to 1714.

Operating on Tuesdays, Wednesdays, and Thursdays, the society maintains an extensive collection of records, documents, and photographs that convey captivating narratives about Ridgefield and its inhabitants.

A major highlight on the calendar is the re-enactment weekend commemorating the Battle of Ridgefield (1777), which occurs annually in late April.

The society also hosts exhibitions at Town Hall and occasionally opens the Peter Parley Schoolhouse for visits.

This structure, located at the corner of West Lane and South Salem Road, was constructed in the mid-18th century and has been preserved to reflect its condition when it ceased operations as a school in the early 20th century.

12. Ridgefield Summerfest

In late July, a Saturday is dedicated to family-friendly activities occurring at multiple venues downtown, including Main Street (closed to vehicular traffic), Lounsbury House, and Ballard Park.

During my attendance, Ridgefield Summerfest featured a multitude of food vendors, sidewalk sales, live musical performances, and an art fair.

Children particularly enjoyed the interactive touch-a-truck event at Lounsbury House, which showcased vehicles from police and fire departments alongside local construction and tree service trucks.

13. Seth Low Pierrepont State Park

The Seth Low Pierrepont State Park serves as a sanctuary for hiking, fishing, and boating, encompassing over 300 acres of stunning, unspoiled landscape interwoven with trails.

Lake Naraneka lies to the west, with its lower portion bordered by the main white-blazed trail. This path curves northward, leading to the highest elevation in the park, where a beautiful overlook awaits.

From Barlow Mountain, one can survey the Redding Hills. On a clear day, the view extends all the way to Long Island Sound. The lake’s banks are equipped with picnic tables, shelters, fishing spots, and a boat launch.

14. Hammond Museum and Japanese Stroll Garden

Crossing into North Salem, New York, visitors can reach this museum dedicated to Japanese and global art, featuring a seven-acre Japanese stroll garden.

During my review, I discovered various concurrent exhibitions, with Mitche Kunzman’s Purgatory, showcasing haunting abstract landscapes, being particularly memorable.

The museum boasts a rich permanent collection, recently augmented by two significant Masami Kodama sculptures in marble.

The Stroll Garden is an essential aspect of any visit. Along the winding path, you’ll experience a multi-sensory journey.

Listen to the sound of pebbles underfoot, inhale the fragrance of katsura trees in early autumn, feel the pine needles brush against your skin, and feast your eyes upon the constant visual wonders throughout.

15. Saugatuck Reservoir

The expansive Saugatuck Reservoir, established by the Bridgeport Hydraulic Company in 1938, spans 827 acres and borders Devil’s Den Preserve to the east.

This tranquil and relatively undiscovered area is currently owned by Aquarion Water Company and is cherished for its fishing opportunities.

The reservoir is stocked with trout, while several species thrive in its natural environment, including bullhead catfish, largemouth bass, white perch, yellow perch, crappie, and walleye, which were noted during my report.

Fishing is permitted along the serene wooded banks from April to December, provided individuals acquire a permit from Aquarion and possess a Connecticut fishing license, both of which are easily obtainable from local civic buildings or bait and tackle shops.

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