15 Best Things to Do in Fairfield (CT)

An affluent town on Connecticut’s Gold Coast, Fairfield is blessed with some alluring beaches on Long Island Sound, as well as old neighbourhoods on quaint town greens.

In summer, Jennings Beach is a joyous place to while away a sunny day, visited by food trucks and organising family film screenings, normally on Friday nights.

Fairfield University is responsible for the Quick Center for the Arts, laying on a programme of live performances and talks by cultural luminaries.

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.

On the programme in Summer 2019 were family movies like Guardians of the Galaxy vol. 2, How to Train Your Dragon 3 and Incredibles 2. As with all the beaches in Fairfield non-residents will be charged a fee to use the parking lot between Memorial Day and Labor Day.

Then outside the summer season, Jennings Beach is one of the best places in the town to take your dog.

There have been some complaints about expensive parking, so you might want to check that before you go.

2. Fairfield Historic District

Fairfield’s old town centre 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, many of which 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 and was the home of two successive congressmen at the turn of the 19th century (Jonathan Sturges and his son, Lewis Burr Sturges).

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 theatre on the Town Green.

When this list was compiled in July 2019 there was a display documenting 375 years of the Fairfield neighbourhood of Black Rock, and Make Your Mark in the Spaght Gallery explored all the ways that artisans like silversmiths, quilters and painters, as well as graffiti and tattoo artists have left their mark on their communities.

In the Tulloch Library Gallery there was also an absorbing show on the flight pioneer Gustave Whitehead, who conducted powered flights in Fairfield and Stratford in 1901 and 1902. The Fairfield Historical Society manages an array of local properties, like the David Ogden House, a saltbox house from 1750, 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, another enticing ribbon of sand, covering 3.5 acres and furnished with lots of facilities.

Washed by the gentle Long Island Sound, the sand at Penfield Beach is soft and cleaned meticulously in summer, and complemented by a swing sets, lockers, a big covered deck, picnic tables and grills to be used on a first come, first served basis.

On a sombre but also hopeful note, Penfield Beach is furnished with a play area built as part of The Sandy Ground: Where Angels Play project honouring the victims of 2012’s Sandy Hook shooting.

The playground at this beach 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 and is embedded in more than 170 acres of parkland.

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 organises 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 cool little ones off and keep them entertained 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.

6. Fairfield University Art Museum

For a blast of high culture Fairfield University has a superb little 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 hal is the university’s captivating collection of historic plaster casts of important works of sculpture from Ancient Greece and Rome, including pieces from the Parthenon.

There’s also a display of African masks, pre-Columbian vessels and sculpture from South East Asia, as well as a remarkable facsimile of the Book of Kells, an illuminated manuscript, produced at a Columban monastery in Britain or Ireland in the 9th century CE.

7. The Warehouse at FTC

Run by the Fairfield Theatre Company, this small but well-equipped venue in the middle of Fairfield has an industrial ambience but comes with state-of-the-art staging, sound system and construction.

The Warehouse can hold up to 640 people and is a fantastic space for live music.

Some of the bands and solo artists to have made a stop at The Warehouse in the last few years are SOJA, Matt Nathanson, Buckethead, The Motet, The Magpie Salute, Tom Tom Club and Average White Band.

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 centre has a rich programme of theatre, 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, and is the home of the Mendelssohn Choir of Connecticut and the Live Music Project, a conductor-less orchestra.

Also on the calendar are regular screenings from the The Met and London’s National Theatre, as well as riveting talks as part of the university’s Open Visions programme.

In September 2019 director Spike Lee was invited to discuss the social impact of Do the Right Thing (1989) for this series.

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.

Maybe the most charming feature is the teaching bridge and its pavilion set on the bend to let you 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

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 and free, but from Memorial Day to Labor Day only residents with a special beach sticker will be able to park in the beach’s lot.

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 neighbourhood 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 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, dating the 1890s and 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, with activities for all members of the family and inviting crafters from across New England.

12. Rock Climb Fairfield

A highly-rated indoor climbing gym, Rock Climb Fairfield was being enhanced with a bouldering experience when we wrote this article in summer 2019. If you’re a first-timer or have only limited experience you can tackle the wall with the help of a qualified belayer for $25 an hour.

Open climb sessions for novices take place Monday, Wednesday, Friday and Sunday and 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 and make 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 burnt down in 1705). There’s an upper and lower pond, both with steep banks from quarrying, giving 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, marsh and even a bog edged with raspberry bushes, dogwood, buttonbrush and multiflora rose.

You can check out Perry’s Mill Ponds on three separate trails, and the main yellow trail traces the Mill River from the entrance and leads you 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 centres on a pond that attracts heron, geese and other waterfowl, as well as the occasional deer to drink 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 nigh on 50 years the Westport Astronomical Society has shined a light on the wonders of the night 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 20:00 and 22:00 provided the sky is clear.

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.

The WAS also schedules free monthly lectures and events with speakers from important institutions like MIT, Yale, Columbia, NYU and the Hayden Planetarium.