An affluent town on Connecticut’s Gold Coast, Fairfield is blessed with some alluring beaches on Long Island Sound, as well as old neighborhoods on quaint town greens.
In summer, Jennings Beach is a joyous place to while away a sunny day. The shore here is visited by food trucks and there are family film screenings on Friday nights.
Fairfield University is responsible for the Quick Center for the Arts, laying on a program of live performances and talks by cultural luminaries.
A personal highlight for me is the downtown, where eateries and unique shops sit close to an18th-century townscape.
The Fairfield University Art Museum also deserves a detour for its Renaissance and Baroque art, and plaster casts of ancient sculptural masterpieces.
Let’s explore the best things to do in Fairfield:
1. Jennings Beach
On a gentle curve the pristine Jennings Beach is long, wide and backed by quiet residential areas. The beach faces east, and at its very north is bordered by a fishing pier at the mouth of Ash Creek.
It’s a gorgeous place to pass a few hours in the summer and is lapped by calm, shallow waters that children can enjoy in safety.
On summer nights there’s often something fun happening at Jennings Beach, like the regular Sand Jam Family Dance. This is followed by a movie screening, so bring a blanket and picnic.
Now, if there’s a drawback it’s that you need a residents beach sticker to use the parking lot, or pay an exorbitant fee. I’d even consider parking downtown to get around this.
2. Fairfield Historic District
Fairfield’s old center is on a stretch of the Old Post Road between Turney Road and U.S. Route 1.
The district was placed on the National Register of Historic Places in 1971 and is composed of an ensemble of 75 historic buildings. I get a little thrill to think that many have been here since the 18th century.
There’s the town hall, crested by a cupola, as well as a typical New England Town Green, the public library and a variety of handsome old houses.
At No. 1 Town Hall Green is the Rising Sun Tavern, dating back to 1783, while the Silliman House, at 543 Old Post Road is from 1791. This was the home of two successive congressmen at the turn of the 19th century (Jonathan Sturges and his son, Lewis Burr Sturges).
Fairfield has a small but thriving downtown along U.S. Route 1, with a concentration of upscale restaurants and boutiques between Beach Road and Ruane Street.
3. Fairfield Museum and History Center
Right by the Town Green is a local museum with temporary exhibitions opening a window on Fairfield’s past.
The Fairfield Museum and History Center is made up of a museum building with several galleries, a research library and reading room, and an 80-seat theater on the Town Green.
I paid a visit during spooky season for the thought-provoking Dearly Departed: Mourning & Memory. This wonderful exhibition explored how people in the area have confronted mortality, with art, costumes, artifacts and ephemera.
The Fairfield Historical Society manages an array of local properties, like the David Ogden House, a saltbox house from 1750. This building is open Sunday afternoons from the start of June to the end of September.
4. Penfield Beach
Travel south along Jennings Beach and you’ll soon find yourself on Penfield Beach. It’s another enticing ribbon of sand, covering 3.5 acres and furnished with lots of amenities. If you’re on foot, I reckon you can get to this spot in 20 minutes from the downtown area.
Washed by the gentle Long Island Sound, the sand at Penfield Beach is soft and cleaned meticulously in summer. The beach is complemented by a swing set, lockers, a big covered deck, picnic tables and grills to be used on a first come, first served basis.
On a somber but also hopeful note, Penfield Beach is furnished with a play area built as part of The Sandy Ground: Where Angels Play project. This honors the victims of 2012’s Sandy Hook shooting, and the playground here celebrates the life of Jessica Rekos.
5. Lake Mohegan Recreation Area
If you’re reluctant to swim in Long Island Sound, the calm and clean Lake Mohegan is a real alternative. It’s all embedded in more than 170 acres of parkland reclaimed from farms and a gravel mine.
The expansive sandy beach is supervised by lifeguards in the summer, and there’s a roped swimming area marking out the depths.
Fairfield Parks and Recreation organizes swimming lessons for children in these waters, beginning with children aged four.
Right by the shore is a children’s sprinkler park with misters and spouts that will keep little ones cool on hot days.
Around the lake there’s some great hiking to be done on marked trails (dogs can go off-leash), guiding you over creeks and past little waterfalls. I’d wear some sturdy shoes here, as the terrain can be a little rugged.
6. Fairfield University Art Museum
For a blast of high culture Fairfield University has a superb art gallery on the lower level of the palatial Bellarmine Hall, which dates to 1921. These galleries are open Tuesday to Thursday in summer, and Tuesday to Saturday for the rest of the year.
You can view Italian Renaissance and Baroque painting in the Meditz Gallery, designed like an early-Christian basilica.
To the side of this hall is the university’s captivating collection of historic plaster casts of important works of sculpture. These range from Ancient Greece and Rome, and include pieces from the Parthenon.
There’s also a display of African masks, pre-Columbian vessels and sculpture from South East Asia. I was blown away by the facsimile of the Book of Kells, an illuminated manuscript, produced at a Columban monastery in Britain or Ireland in the 9th century CE.
Something that caught my eye on the Bellarmine Lawn was a series of larger-than–life sculptures depicting leaves from New England trees. Produced by Alan Sonfist, these represent a beech, oak, maple and chestnut, and serve as a call for conservation awareness.
8. Quick Center for the Arts
The cultural heart of Fairfield University, the Quick Center for the Arts was founded in 1990 and can hold audiences of 740. The center has a rich program of theater, classical and popular music, dance, talks and shows and activities for children.
The venue receives the Chamber Music Society of Lincoln Center on an annual basis. It’s also the home of the Mendelssohn Choir of Connecticut and the Live Music Project, a conductorless orchestra.
On the calendar are regular screenings from The Met—I took the chance to see Verdi’s Nabucco— and London’s National Theatre. Don’t miss the series of riveting talks as part of the university’s Open Visions program.
Among the luminaries to visit in recent years are director Spike Lee, who discussed the seminal Do the Right Thing (1989).
9. Connecticut Audubon Society Birdcraft Museum and Sanctuary
Founded in 1914 by author and early Audubon movement leader Mabel Osgood Wright (1859-1934), Fairfield has America’s oldest private songbird sanctuary.
In six acres, this comprises a pond and gardens, specially planted to attract birdlife (more than 120 recorded) and butterflies.
To my mind, the most charming feature is the teaching bridge and its pavilion set on the bend. From here you can appreciate the sanctuary’s full beauty.
The museum itself houses vintage dioramas with mounted animals, presenting Connecticut’s biodiversity as it was in the early 20th century.
Of the many programs, Naturalist Training is an eight-week course to help you become even more knowledgeable about Connecticut’s flora and fauna.
10. Sasco Beach
West of Kensie Point and just south of the Country Club of Fairfield, this 10-acre beach is a much more remote and tranquil option compared to the beaches above.
Sasco Beach is a public beach, but it comes with a caveat. When I wrote this article, only residents with a special beach sticker were able to park in the beach’s lot between Memorial Day Weekend and Labor Day.
There’s a wide patch of pale sand on calm water, and to the rear is the open greenery of the Country Club of Fairfield’s golf course. Linger until the evening to watch the sun going down behind Southport.
To mix things up, a little way east of Sasco Beach is the Carl Dickman par 3 public golf course.
11. Greenfield Hill Historic District
A couple of minutes out of Fairfield proper, the affluent neighborhood of Greenfield Hill has a very picturesque historic district, all set around a classic New England green.
The district is on the National Register of Historic Places and is made up of 27 contributing buildings across 175 acres.
The most eye-catching of these for me is the whitewashed Greenfield Hill Congregational Church beside the green and established in 1725.
Timothy Dwight Park is the former site of an academy run by the influential Congregationalist minister and eighth president of Yale, Timothy Dwight IV (1752-1817). Also in the district is the Bronson Windmill, with an octagonal wood frame. This dates from the 1890s and is the last of many such mills on the Fairfield skyline.
Every May for almost a century Greenfield Hill Church has hosted the three-day Dogwood Festival. This has activities for all members of the family and invites crafters from across New England.
7. The Warehouse at FTC
Run by the Fairfield Theatre Company, this well-equipped venue in the middle of Fairfield is a pillar of the local cultural scene. There’s a stripped-back industrial design here, paired with state-of-the-art staging, sound system, and acoustics.
The Warehouse can hold up to 640 people and shines as a space for live music. An impressive roll-call of major performers to have made a stop at The Warehouse in the last few years.
To name a few, you’ve got The Feelies, SOJA, Matt Nathanson, Buckethead, The Motet, The Magpie Salute, Tom Tom Club, and Average White Band.
12. Rock Climb Fairfield
A highly-rated indoor climbing gym, Rock Climb Fairfield was being enhanced with a bouldering experience in the late 2010s. If you’re a first-timer or have only limited experience you can tackle the wall with the help of a qualified belayer for an hourly rate.
Open climb sessions for novices took place Monday, Wednesday, Friday and Sunday when I wrote this article. These may require advanced booking because they’re limited to 12 climbers.
If you have some climbing experience under your belt and can prove it by tying a figure of eight knot and belaying properly, you can buy a day pass. This gives you full use of the gym’s top rope, lead climb and new bouldering terrain.
Rock Climb Fairfield also provides certification courses and classes for those who want to take their hobby to the next level.
13. Perry’s Mill Ponds Open Space Area
At this natural space you can trace a reach of the Mill River and see how human hands have reshaped the watercourse and ecology.
Up until the settlement of Europeans the river flowed to Long Island Sound unobstructed, but that changed with mills, dams and quarries.
Perry’s Mill Ponds are partly the consequence of 20th-century gravel extraction for road projects like the I-95 and Merritt Parkway. But there’s also evidence of a dam for Perry’s Mill, dating right back to 1680 (the mill burned in 1705).
There’s an upper and lower pond, both with steep banks from quarrying. This gives rise to a level of biodiversity not seen in other natural spaces in Fairfield.
In the higher areas there’s upland forest of oak, black birch and beech, and further down there’s open water and marsh. In these lower portions you’ll find a bog edged with raspberry bushes, dogwood, buttonbush and multiflora rose.
You can check out Perry’s Mill Ponds on three separate trails. My starting point is the yellow trail, tracing the Mill River from the entrance and leading to the two ponds.
14. Gould Manor Park
This blissful local park is buffered from the I-95 by a thicket and steep bank.
Gould Manor Park centers on a pond attracting heron, geese and other waterfowl. Occasionally I’ve seen deer come to drink here when there are fewer people around.
From the water’s edge you’ll see lots of turtles, and every April 1 the pond is stocked with trout for a fishing derby for children aged 3 to 15. The play areas are well-looked after and have equipment for toddlers and bigger kids.
The south side of the pond, enclosed by tall trees, is the idyllic location for a Little League field.
15. Westport Astronomical Society (WAS)
For 50+ years the Westport Astronomical Society has shined a light on the wonders of the night sky for thousands of visitors.
Their observatory, just across the town line from Fairfield, has a 16′ Meade LX200 telescope with an Explore Scientific 102mm f/7 Essential Apochromatic ED Triplet Refractor on top.
You can come to peer through this instrument on Wednesday nights between 8:00 PM and 10:00 PM. Naturally the experience is weather permitting.
On some nights the whopping 25′ Obsession telescope will be brought out onto the lawn. This is the largest telescope available to the public in Connecticut, and it’s something no stargazer will want to miss.
The WAS also schedules free monthly lectures and events with speakers from important institutions like MIT, Yale, Columbia, NYU and the Hayden Planetarium.