15 Best Things to Do in Ridgefield (CT)

An hour out of NYC at the foot of the Berkshires is a 300-year-old town with an upscale air.

Ridgefield lays claim to the only national park in the United States devoted to the arts. This is the home and studio of the Impressionist J. Alden Weir, and one of my favorite spots, anywhere in New England.

Another key figure in American culture, architect Cass Gilbert, had a summer home at Ridgefield’s historic Keeler Tavern. Today it’s kept as a museum, and is not to be missed.

There are boutiques and restaurants aplenty on the picture-perfect Main Street. Downtown Ridgefield also has cultural venues of high standing like the Aldrich Contemporary Art Museum, and the Ridgefield Playhouse.

1. Keeler Tavern Museum and History Center

Steeped in history, the Keeler Tavern was first built in 1713 and was caught up in the Battle of Ridgefield in 1777. The landlords at the time, Timothy and Ester Keeler, had revolutionary sympathies, and for that reason the inn was fired upon by British troops.

I was amazed to find one of the British cannonballs is still visibly stuck in a corner post more than 240 years later.

Cass Gilbert (1859-1934), the architect behind the Woolworth Building and Supreme Court Building, used the property as a summer home from 1907. He made additions and plotted the current garden.

The museum is filled with period furniture, art and ceramics from the 18th century to the 20th century to reflect the changing lifestyles of its occupants.

Some of the standout pieces in the collection are an original engraving of the Battle of Ridgefield, the original inn sign, and family portraits. Look out for the broadside of Columbus, an elephant that came to the tavern at the start of the 19th century.

2. Weir Farm National Historic Site

In Ridgefield you can visit the home and studio of the celebrated Impressionist painter J. Alden Weir (1852-1919).

Weir called his property, amid 60 acres of woodland, field and waterways, the “Great Good Place”.

What makes this such an important site for American culture is the number of important painters who stayed at Weir Farm. Among them are Albert Pinkham Ryder, Childe Hassam, John Twachtman and John Singer Sargent.

Weir Farm was Alden’s summer home from 1882 to 1919, and he and his famous contemporaries would experiment with light and color to create enduring masterpieces.

Weir Farm is America’s only national Park devoted to Impressionist painting. To me, its main appeal lies in the dainty gardens and rural landscapes immortalized by Weir, Sargent and the like.

You can take a tour of the Weir House, Weir Studio and Young Studio, either with a guide or at your own speed.

Naturally, a big schedule of art classes is held in this inspiring place. You can also grab a set of the free-to-use art supplies at the visitor center porch between May and October to paint your own masterpiece.

3. Ridgefield Playhouse

This splendid performing arts venue is actually adapted from the old Ridgefield High School’s auditorium.

The building was raised in the late-1930s and designed by Cass Gilbert Jr. It was converted into a 500-seater theater in 2000, and barely has an empty night on its calendar.

The program brims with concerts by music artists from a variety of genres, together with comedy, dance, and movie screenings. There are also recordings from institutions like London’s NT and conversations and talks with some famous cultural figures.

Jim Norton, Patti LuPone, David Sedaris, Alan Ruck, and Madeleine Peyroux were all booked when I put this article together.

4. Aldrich Contemporary Art Museum

Established in 1964, this respected independent art museum gives a platform to innovative young or under-appreciated artists whose interpretations of the world help foster creative thinking.

The Aldrich has no permanent collection, and instead hosts the first exhibitions for emerging talent. You can also catch shows for artists in the middle of their careers who haven’t yet found a large audience.

The list of groundbreaking artists to have featured at the Aldrich is formidable. It includes Frank Stella, Cy Twombly, Robert Rauschenberg, Olafur Eliasson, Eva Hesse, and Jasper Johns.

When I came, I was enthralled by Chiffon Thomas’s otherworldly, politically charged installations.

The museum’s programs are designed to engage people of all ages with contemporary art. So look out for expert presentations, tours, and workshops.

5. Main Street

Something that puts Ridgefield among Connecticut’s best towns is its elegant main thoroughfare. This is packed with charming storefronts and solemn civic architecture.

A quick look at the painted storefronts, trees, shrubs, flowerbeds and fountains, and you’ll know that Main Street is cared for with a lot of pride.

There are local businesses in spades here. I’m talking, a bookshop, toy shop, florist, jewelry store, lingerie shop and a clutch of fashion boutiques and design stores.

The dining selection will send you around the world in the space of a block or two, with Mexican (Baja Cocina), French bistro fare (Luc’s Café), and pizza (850 Degrees). There’s also a smattering of specialty shops, cafes, a hotdog stand, a tavern, and a lot of options for live entertainment.

Opposite Ridgefield Library on Main Street is Ballard Park, which has neat formal gardens in five acres. It’s the go-to for outdoor events and concerts on warm summer evenings, and I’ll talk about one later.

6. Prospector Theater

I found so much to love about this sleek, first-run movie theater in Ridgefield. The Prospector Theater is a non-profit enterprise set up to provide employment experience for people with disabilities.

You’ll find it just off Main Street, surrounded by Ridgefield’s contingent of restaurants.

There are four screens here, with two on the main floor, one upstairs with bean bags and Eames lounge chairs, and an intimate little room in the basement.

There are concessions in the lobby of course, and a cafe pouring beer and wine by the glass. Opened in 2014, the theater has eye-catching design inside and out, and a superlative sound system.

7. ACT of Connecticut

A Contemporary Theatre of Connecticut (ACT) is a recently founded producing theater at 36 Quarry Road in Ridgefield, putting on Broadway-style productions in limited runs.

When I was in town, some of the shows coming up included Sunset Boulevard, Kinky Boots, and Million Dollar Quartet. These were combined with brand new musicals and plays, seasonal programming, a popular annual gala in June, and much more.

Each production mixes Broadway professionals with local talent from Fairfield and Westchester Counties.

Together with its performances, ACT also runs a conservatory program and offers workshops, camps and youth education classes.

8. Lounsbury House

Setting the upmarket tone in the heart of Ridgefield is this fine mansion, built in the Classical Revival style in 1895. Lounsbury House was commissioned by the 53rd Governor of Connecticut, Phineas C. Lounsbury (1841-1925).

The design is in fact modeled on the Connecticut State Building show at the 1893 Columbian Exposition in Chicago.

The building was gifted to the town in 1945, and since then has been a venue for private and public events. I’d look out for the Music at the Mansion series, with high-quality chamber music performances.

9. Devil’s Den Preserve

Spread out over more than 1,750 acres, Devil’s Den is the largest Nature Conservancy preserve in Connecticut. In fact it’s one of the larger preserves in the Metropolitan New York Area.

There are 20 miles of trails in this thickly wooded landscape, taking in wetlands, a gorge, an 18th-century millpond, streams and lofty ridges granting distant views.

Most memorable for me were Ambler Gorge and its rugged cascade, and the soaring rock formation at Great Ledge.

Devil’s Den is a habitat for over 500 types of tree and wildflower. Among the blooming plants are Indian pipe, cardinal flower and pink lady’s slipper.

Animal species include bobcats, red foxes, coyotes and eastern copperhead snakes, as well as more than 140 bird species.

10. Pine Mountain/Hemlock Hills

If you love nature as much as I do, there’s a cluster of marvelous open spaces in the north of Ridgefield. These all merge together to form a huge parcel of wilderness, with rolling hills, fields and scenic overlooks.

Roughly speaking, the eastern portion is the 368-acre Pine Mountain Reserve while to the west are the Hemlock Hills.

Three large bodies of water make up the southern boundary, at Lake Windwing, Rainbow Lake and Bennett’s Pond. The latter is in a state park.

Some of Ridgefield’s highest points are on this land, and you make your way through this hilly woodland on a series of trails.

A red-blazed trail links the Hemlock Hills with Pine Mountain, while the red and yellow blazed Ives Trail goes from Bennett’s Pond to the Hemlock Hills. These pass locations relevant to the famed 20th-century composer, Charles Ives.

11. Ridgefield Historical Society

You can do a deep dive on Ridgefield’s 300-year past at the Ridgefield Historical Society, which is based at the Scott House, dated to 1714.

Open Tuesday, Wednesday and Thursday, the society keeps a huge collection of records, documents and photographs. These all help to tell engaging stories about Ridgefield and the people who have lived here.

My calendar highlight is the weekend of re-enactments marking the Battle of Ridgefield (1777), every year in late April.

You can also check out exhibitions by the society at the Town Hall. Also, from time to time the Peter Parley Schoolhouse is open for visits.

At the corner of West Lane and South Salem Road, this building went up in the mid-18th century. It has been preserved as it was when it closed as a school at the start of the 20th century.

12. Ridgefield Summerfest

On a Saturday in late July there’s a day of family fun, with something happening at various locations downtown. These are Main Street (closed to road traffic), Lounsbury House and Ballard Park.

When I attended, Ridgefield Summerfest included numerous food vendors, sidewalk sales, live music performances, and a mini art fair.

Kids are sure to have a great time, not least because of the touch-a-truck event at Lounsbury House. On display were police and fire department vehicles, as well as local construction and tree service trucks.

13. Seth Low Pierrepont State Park

A haven for hiking, fishing and boating, the Seth Low Pierrepont State Park is more than 300 acres of breathtaking, unblemished scenery coursed by trails.

To the west is Lake Naraneka, the lower half of which is hugged by the main, white-blazed trail. This bends north and climbs to the highest point in the park at a beautiful overlook.

At Barlow Mountain I could see across the Redding Hills. Pick a clear day, and you can see as far as Long Island Sound. On the banks of the lake are picnic tables and shelters, fishing berths and a boat launch.

14. Hammond Museum and Japanese Stroll Garden

Cross the state line into North Salem, New York and in a few short minutes you’ll come to this museum for Japanese and world art paired with a seven-acre Japanese stroll garden.

When I compiled this there were several concurrent exhibitions. The pick of these for me was Mitche Kunzman’s Purgatory, with its haunting abstract landscapes.

This was all matched by a rich permanent collection that has recently been bolstered by two important Masami Kodama sculptures in marble.

The Stroll Garden is integral to any visit. Along a circuitous path you’ll journey through a multi-sensory space.

You’ll hear the sound of pebbles underfoot, catch the scent of katsura trees in early autumn, feel pine needles brush against your skin, and delight in constant visual beauty throughout.

15. Saugatuck Reservoir

Devil’s Den Preserve is bordered to the east by this large reservoir, 827 acres in size and established by Bridgeport Hydraulic Company Holdings in 1938.

It’s a serene and unfrequented place, now owned by the Aquarion Water Co., and treasured for its fishing opportunities.

The water is stocked with trout and has large natural populations of several species. Bullhead catfish, largemouth bass, white perch, yellow perch, crappie and walleye, were a few when I wrote this list.

You can fish on the peaceful wooded banks from April to December, but you’ll need a permit from Aquarion and a Connecticut fishing license. Both are easy to obtain from civic buildings or from bait & tackle shops in the area.