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, at the home and studio of the Impressionist J. Alden Weir.
Another key figure in American culture, architect Cass Gilbert, had a summer home at Ridgefield’s historic Keeler Tavern, which is kept as a museum.
There are boutiques and restaurants aplenty on the picture perfect Main Street, and 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.
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, making additions and plotting a 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, family portraits and a 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, including 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 colour to create enduring masterpieces.
Weir Farm is America’s only national Park devoted to Impressionist painting, and its main appeal lies in the dainty gardens and rural landscapes immortalised 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.
Art classes are held in this inspiring place, and you can 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 theatre 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, movie screenings, recordings from institutions like London’s NT and conversations and talks with some famous cultural figures.
Graham Nash, David Sedaris, Rick Wakeman, Gordon Lightfoot, Ken Jeong, Jeffrey Tambor and Sophia Loren were just a few of the big names booked for shows or talks in autumn and winter 2019-20.
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 artists, as well as 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 and includes Frank Stella, Cy Twombly, Robert Rauschenberg, Olafur Eliasson, Eva Hesse and Jasper Johns.
The museum’s programs are designed to engage people of all ages with contemporary art through expert presentations, tours and workshops.
5. Main Street
One of the things that puts Ridgefield among Connecticut’s best towns is its elegant main thoroughfare, with stately houses and solemn civic architecture.
A quick look at the painted storefronts, trees, shrubs, flowerbeds and fountain, and you’ll know that Main Street is cared for with a lot of pride.
There are local businesses in spades here, and just off the main drag, at a bookshop, toy shop, florist, jewellery 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), contemporary Asian (Yuan Asian), pizza (850 Degrees, Planet Pizza) and a smattering of speciality shops, cafes, a hotdog stand, a tavern and a diner.
Opposite Ridgefield Library on Main Street is Ballard Park, which has neat formal gardens in five acres and is the go-to for outdoor events and concerts on warm summer evenings.
6. Prospector Theater
There’s 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 new producing theatre at 35 Quarry Road in Ridgefield, putting on Broadway-style productions in limited runs.
The first season had sold-out runs for Evita, Mamma Mia!, Working, Austen’s Pride and The 25th Annual Putnam County Spelling Bee.
At the time of writing in summer 2019, some of the shows on the horizon for the 2019-20 season were Little Shop of Horrors, Godspell, Nickel Mines and Freaky Friday.
Each production mixes Broadway professionals with local talent from Fairfield and Westchester Counties.
Together with these shows, ACT also runs a conservatory program and offers workshops, camps and youth education classes.
8. Garden of Ideas
This endearing non-profit attraction has 12 acres of cultivated and wild gardens, marshland and woodland.
There’s dramatic outdoor sculpture, a wonderful diversity of garden styles, a boardwalk through the wetland, a small indoor gallery and abundant plant life grown in farm lots.
Head to Garden of Ideas for inspiration on organic gardening, bird-spotting and to plenty of imaginative art.
The farm stand sells freshly laid eggs in season, as well as vegetable and ornamental plants, and handmade garden decorations like gnomes, Buddhas and gargoyles.
9. Devil’s Den Preserve
Spread out over more than 1,750 acres, Devil’s Den is the largest Nature Conservancy preserve in Connecticut, and 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 are 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, and 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
In the north of Ridgefield there’s a cluster of open spaces that 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, which 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, passing 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 to tell engaging stories about Ridgefield and the people who have lived here.
You can also check out exhibitions by the society at the Town Hall, and on the last Sunday of the month from May to October 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 and has been preserved as it was when it closed as a school at the start of the 20th century.
12. Saltana Cave
A wellness experience completely out of the ordinary, Saltana Cave in Darien is a chamber lined with many tons of Himalayan pink salt, on the ceiling, walls and floor, accompanied by a large, shimmering brine cascade.
This pharmaceutical salt has been chosen for its anti-inflammatory, antibacterial and antimicrobial properties.
As well as providing relaxation, the pure dry salt vapor is thought to soothe skin ailments and ease respiratory problems.
The main treatment offered at Saltana Cave is speleotherapy (salt cave therapy) but the owners are also introducing halotherapy using a salt generator.
The cave is open Tuesday through Saturday, taking bookings at $40 per session, with discounts for multiple session packages.
13. Seth Low Pierrepont State Park
A haven for hiking, fishing and boating, the Seth Low Pierrpont 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 that then bends north and climbs to the highest point in the park at a beautiful overlook.
At Barlow Mountain you can see across the Redding Hills and as far as Long Island Sound if you pick a clear day.
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 we compiled this list in August 2019 there were four concurrent exhibitions: Works by master potter Jay Lindsay; paintings and monotypes by artist Richard Jacobs; pieces by acclaimed artist Elisa Pritzker inspired by the native Argentine Selknam tribe, and finally an outdoor sculpture display, Full Bloom.
This is all matched by a rich permanent collection that has just been bolstered by two important Masami Kodama sculptures in marble.
The Stroll Garden is integral to a visit, and along a circuitous path you’ll journey through a multi-sensory space to 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 the visual beauty of the garden as a whole.
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 plenty of bullhead catfish, largemouth bass, white perch, yellow perch, crappie and walleye, to name a few.
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.