Things to do in Fairfield CT: Top 24 Most Unique

Fairfield, Connecticut is rather sly. At first glance, it’s just another town in Connecticut suburbia. But over time, exploring the many things to do in Fairfield CT, you’ll find more and more to keep you visiting.

The former capital of Fairfield County, you’ll find markers all along the Post Road indicating your distance from Fairfield.

It’s enjoyed a resurgence despite fearmongering from GE’s departure about a decade ago. And fears before that about it losing its title of the county’s seat of government.

After all, this adorable town on Connecticut’s Gold Coast has a lot going for it. It has five fantastic beaches and is brimming with New England charm.

And Fairfield, CT is without question a college town. Fairfield University adds so much to the cultural scene, from art galleries to performing arts venues.

So read on for our list of the best things to do in Fairfield CT.

Top Things to do in Fairfield, CT

Whatever your interests are, use our list of the best things to do in Fairfield, Connecticut, to plan a fun day out.

Map design by Stanton House Inn with elements from Flaticon

Historic Sites in Fairfield, CT

As with all Connecticut towns, Fairfield has a long past. And the:

Ancient burial grounds
Historic greens
And colonial homes

Sprinkled throughout town bear testament to it.

Fairfield Historic Districts

Fairfield has three historic Connecticut districts. Two are well worth a visit, especially the cuter of the two.

Old Post Road Historic District

The cutest historic district is along Old Post Road. This charming location serves up a tasty dose of history in an enticing package. Leave the car in a nearby parking lot and walk to appreciate the area’s historic charm.

The Old Town Hall, topped by a cupola, stands alongside a typical New England Town Green, the public library, and many elegant old homes. The district, which consists of 75 historic structures, was added to the National Register of Historic Places in 1971. Many of these structures date from the 18th century.

Kids’ Cottage, and the Sun Tavern (built around 1780) are here. A well-preserved 1888 Victorian Cottage and Barn is on the Town Green behind the Fairfield Museum and History Center. Inside, interactive exhibits highlight the town’s agricultural heritage as well as current farming trends.

Take advantage of a self-guided tour with informative signs placed throughout the area. Did you know that colonists in Connecticut hid their colonial charter in an oak tree to protect it from the royal governor, Edmund Andros? The tree was later given the name Charter Oak.

And that is why our state tree is a Charter Oak. Not a species of oak, a specific one that’s no longer standing.

This area also contains the Fairfield Honor Roll, a memorial built in memory of those who served in:

World Wars I and II
The Korean War
Vietnam
And the Persian Gulf

In 1804 the charming Fairfield Academy opened its doors on the grounds. The school closed 80 years later as a result of the popularity of nearby free schools. Today, the replica classroom is a reminder of a bygone era.

Greenfield Hill Historic District

The Greenfield Hill Congregational Church is at the heart of the Greenfield Hill Historic District. This church adds classic New England charm and history to this historic neighborhood. Its 1855 steepled building is easy to find with baby-blue doors and a clean, white interior.

This wonderful location, which has been on the National Register of Historic Places since 1971, should not be missed. Greenfield Hill is home to magnificent mansions owned by the town’s elite.

It also hosts other such historic remnants as the lovely 105 Meetinghouse Lane. This grand, privately owned house was built in the mid-eighteenth century. The Old Salt Box is another adorable private home, built in 1751.

Bear in mind that all these homes are private property, but you can view them from the road.

Park at the church and stroll along the open, tree-lined streets to appreciate the area’s allure.

Another historic site here is the Greenfield Hill Cemetery on Bronson Road. It was formerly an Indian Burial Ground, and contains the graves of soldiers who fought in the Revolutionary, French, Indian, and Civil Wars. Some of the region’s earliest inhabitants are also buried there.

Ogden House Museum & Dooryard Garden

The Ogden House Museum and Dooryard Garden are managed by the Fairfield Museum and History Center, which is 2.5 miles to the northwest.

This charming cottage is a former saltbox-style farmhouse built around 1750. The Ogden family once owned it.

The house survived fires the British started here during the American Revolutionary War.

Today, it is furnished with:

Period-appropriate furniture
Glassware
And other daily necessities of the Revolutionary era

The Fairfield Garden Club maintains the Colonial Kitchen Garden, also known as the Dooryard Garden, in the backyard. The garden contains staples for European colonists:

Fruits
Vegetables
And herbs

Along crushed seashell walkways. The plants here produced dyes, medicines, and insecticides, among other things.

Fairfield Museum and History Center

As with all small towns in Connecticut, Fairfield has an impressive history museum.

This large structure on the historic Town Green houses a variety of exhibitions about Fairfield’s past. It debuted in 2007.

The diverse exhibits at the Fairfield Museum and History Center aim to educate about:

The region’s history
Celebrate their common heritage
And foster a sense of community

The museum is home to a sizable research library where guests can learn even more about Fairfield County’s past from 1639 to the present. Join a guided walking tour of “Old Post Road,” “Town Green,” or “East Cemetery” or go to one of the free Jazz Friday performances taking place outdoors in August.

Some more attractions include:

Interactive areas to inspire children
A wigwam
And learn about the town’s history as a “charming summer resort.”

Penfield Reef Lighthouse

The Penfield Reef Lighthouse is on a small artificial islet off the coast of Fairfield.

Built in 1874, this historic lighthouse served as an important landmark for sailors traveling along Long Island Sound.

There were many mishaps here, most notably a string of Blue line barges getting stuck on the reef. And that was even with a lighthouse here.

The lighthouse has a reputation for being one of the most haunted places in CT.

Locals report seeing the ghost of the lighthouse’s former keeper wandering around the property.

As Penfield Reef Lighthouse is privately owned, don’t step foot on the island.

That said, you can still see the lighthouse from a distance. And another lighthouse nearby, the Sheffield Island lighthouse in Norwalk, is accessible by ferry.

Black Rock

Black Rock Harbor is a historical site that was once a significant commercial port. This historic neighborhood is just across the Black Rock River from Fairfield in Bridgeport, CT.

Its seaside park, Saint Mary’s by the Sea, served as a port for trade and shipbuilding in the 1800s.

At this recreational harbor, locals can go fishing, strolling, and sightseeing.

While you’re there, go birdwatching or take a stroll to enjoy the gorgeous views of Long Island Sound.

Downtown Fairfield, CT

Downtown Fairfield, Connecticut is full of:

Name-brand stores
Unique boutiques
And sweets shops

As well as performance spaces and concert halls.

Shopping in Fairfield, Connecticut

The Post Road is the heart of Fairfield’s shopping district. You’ll find everything you need along this long stretch.

The Fairfield University Bookstore is a popular local hangout. The helpful staff here has some great suggestions for readers of all genres. You’ll also find:

A cozy café
A large selection of books (including a fantastic discounted section)
And all Fairfield University merchandise

After you’ve given your brain a workout, visit one of the neighborhood’s adorable cafés or take a break by Sherman Green’s gazebo.

Between May and mid-November, the Fairfield Farmers Market makes Sundays ideal for a visit.

Restaurants in Fairfield, Connecticut

Pizza is a local favorite, which explains why there are so many fantastic pie shops in Fairfield.

Excellent options for the best downtown Fairfield, CT, restaurants include:

Frank Pepe Pizzeria Napoletana
Colony Grill
And Nauti Dolphin Pizzeria

If you want something healthier, go to locally-owned The Stand Vegan Café. It’s on Mill Plain Road and serves the best vegan food in town.

Still hungry? Tapas are so good at local chain Barcelona that you’ll beg for seconds (possibly thirds). And Wild Rice is a Pan-Asian restaurant with a funky interior and consistently good food.

Saugatuck Sweets offers a wide range of ice creams, baked goods, and candy. As its name implies, it’s a local chain originally from Westport, CT. The Fairfield branch is on Reef Road, next to Sherman Green. It’s a great place to unwind and enjoy a treat outside, especially on a summer afternoon.

And Firehouse Deli next door has the best Thanksgiving leftovers sub in Connecticut.

Though I may be biased.

Beaches in Fairfield, Connecticut

Fairfield hosts some of the best beaches in Connecticut.

Jennings Beach

When you visit Jennings Beach, you’ll understand why it’s considered one of Connecticut’s best beaches. There are many iconic white lifeguard stands along its long, broad shoreline.

Families frequently flock to the fine sand for a day of picnicking, sandcastle building, and play. A picnic table is a less-messy place to eat your picnic lunch. And the northern fishing pier makes a beautiful backdrop for creative photographs.

Other amenities like restrooms and a concession stand are available, but you’ll need to bring your chair and umbrellas. Watch boats pass by the lavish cottages that line the nearby shores while you unwind and sit back.

To park here between Memorial Day and Labor Day, only residents can buy a beach pass. A daily pass is available for purchase, but it is expensive enough that you’ll want to make sure you get a full day here.

Penfield Beach

This well-kept secret along Fairfield Beach Road tempts people to spread out across its wide, sandy expanse. With three and a half acres to enjoy, there are plenty of places to spread out your towel, set up a chair, and open your beach umbrella.

This immaculate beach, surrounded by a large pavilion, evokes a 1960s summer beach vacation.

At Penfield Beach, you’ll find:

Kayak and sailboat racks
Picnic tables
Charcoal grills

And children recklessly run around while adults sunbathe on the grounds.

If you don’t want sand in your lunch, go to the picnic tables or seek shade in the pavilion. It’s easy to spend the entire day here with a concession stand, rental lockers, and restrooms on-site.

A small playground is near the entrance. It was built as a memorial to Jessica Rekos, a Sandy Hook victim, and is frequently visited by excited children.

The Sandy Ground: Where Angels Play Project has created 26 play areas across the state to honor Sandy Hook victims, including this one.

Sasco Beach

Because it is a smaller, more private beach than Jennings and Penfield, Sasco Beach is a welcome respite for those looking to unwind. This quiet area, hidden behind the Country Club of Fairfield, is west of Kensie Point. It’s south of Southport Harbor and a lovely spot to watch waves lap the shore.

Although this beach is free and open to the public, only locals with beach stickers can park here from Memorial Day to Labor Day. Non-residents must use another mode of transportation or visit during the off-season. But that’s a real treat because it is less crowded, like most beaches nearby.

This location is quite peaceful and a great place to watch the sunset over Southport.

Parks and Outdoor activities in Fairfield, CT

When it comes to hiking, Fairfield offers more undeveloped, off-road adventure with plenty of options.

Lake Mohegan Recreation Area

This park could go under the list of beaches, but I prefer hiking here to its lakeside beach.

The Lake Mohegan Recreation Area has over 170 acres of lush forest, creeks, waterfalls, and crystal-clear water.

There are many trails in the woods where you and your four-legged friend can go for a walk. This park is dog-friendly, so your dog is bound to make some new friends.

During the summer, sunbathers flock to the artificial freshwater lake and tiny sand beach. Lifeguards keep an eye on the children while they play in the water, dig holes, and picnic with their parents. Due to the lack of shade, a beach umbrella is a must if you intend to spend time in this enjoyable location.

A playground and a sprinkler park are also available for children’s enjoyment. With on-site amenities such as:

A snack bar
Restrooms
And outdoor showers

This family-friendly beach makes it easy to spend the entire day there.

But the coolest thing you’ll find is a cluster of rock formations, waterfalls, and bridges. It feels like something you’d find out West, rather than here in lil’ ol’ Connecticut.

Connecticut Audubon Society Birdcraft Museum and Sanctuary

Mabel Osgood Wright founded the Connecticut Audubon Society in 1898. Her goal was to protect the state’s avian population and natural habitats. In 1914, Annie Burr Jennings donated 10 acres of land to the society. They established the Birdcraft Sanctuary, the nation’s first private songbird sanctuary.

In 1993, the six-acre sanctuary was designated a National Historic Landmark. Here you’ll find the museum, a large pond, butterfly and bird-attracting gardens, and a caretaker’s cottage. This is a truly peaceful, yet welcoming, place to spend a quiet morning or afternoon.

A small lookout offers a closer look at the area’s wildlife, and a wooden walkway circles the pond’s edge. The small museum itself contains exhibits about the local wildlife and their natural habitats. Behind it are several rescued birds, including owls, raptors, and hawks.

Roy and Margot Larsen Wildlife Sanctuary

The 155-acre Roy and Margot Larsen Wildlife Sanctuary surrounds the Connecticut Audubon Society Birdcraft Museum and Sanctuary. During your visit to this natural utopia, you can expect to see a wide variety of animals, including turtles, hawks, and owls.

You’ll discover various ecosystems along the sanctuary’s seven miles of winding trails. A personal favorite are the freshwater ponds and wetlands. Signs throughout the area highlight the area’s history as well as the flora and fauna that you are admiring. This is an excellent place to bring children because there are many short trails.

The Chiboucas trail is wheelchair and stroller friendly, thanks to wooden boardwalks. And viewing platforms make it easy to see wildlife in the wetlands. Be on the lookout for a replica of an Algonquin wigwam.

Gould Manor Park

Gould Manor Park has everything you need for a fun day out. Tennis courts, a large pond, walking trails, a playground, grassy areas, and plenty of fishing are available at this family-friendly local attraction.

While it’s close to I-95, a steep bank, and a thicket protect it from the noise.

The pond is a major draw for those who enjoy the beautiful scenery. It’s a great place to visit for nature lovers and serious birders because it’s home to some of the region’s most beautiful wildlife, such as blue herons, deer, turtles, and other waterfowl.

Those who are lucky enough to be fishing in early April may strike gold because the pond is stocked with trout for the annual Police Athletic League Fishing Derby. The derby, held on a Saturday in early April, is open to children aged three to fifteen.

Depending on how cold the winters are, you can also go sledding here.

Perry’s Mill Ponds

Perry’s Mill Ponds can be found in Fairfield’s geographic center. This charming location consists of a 58-acre open space surrounded by houses.

The Perry’s Mill dam is located on the Mill River, nearly 1,200 feet upstream of the Sturges Road Bridge. This is a popular photographing location and a scenic treat for any visitor.

There is a small lot just off Sturges Road where you can park. Perry Street and Pell Meadow Drive both have on-street parking (for a limited number of vehicles).

The yellow trail begins at the Sturges Road entrance and travels north along the west bank of the river. You’ll also pass by the upper and lower ponds on this path.

Perry Street leads to the blue trail, a 1.2-mile loop that connects Lower and Pickerel Ponds. Pell Meadow Drive leads to the shorter but equally beautiful orange trail.

Arts and culture in Fairfield, Connecticut

As with much of the Gold Coast, Fairfield punches above the belt. Culturally speaking, at least.

Fairfield University Art Museum

The Fairfield University Art Museum (FUAM) is a hidden gem on the university’s campus on the lower level of Bellarmine Hall.

The hall is a work of art in and of itself. Inside, you’ll find a permanent collection of paintings, sculptures, and photographs. Many of the works are by both European and American artists.

There is also a copy of the Book of Kells on display, as well as an impressive collection of ancient plaster casts of artwork from Ancient Greece and Rome.

And yet Western art isn’t the only draw here. African masks, pre-Columbian vessels, and sculptures from South East Asia are also on display.

The Fairfield University Art Museum has ancient and medieval artifacts on loan from:

The Metropolitan Museum of Art in New York
The Yale University Art Gallery
And the Worcester Art Museum

Catch a Concert at The Warehouse at FTC

Unassuming Fairfield hosts concerts ranging from classical to rock. The Quick’s resident Mendelssohn Choir of Connecticut performs at the Warehouse, too. Various types of theater and dance performances are frequently on offer as well.

If you like:

The funk and soul group Average White Band
To dance to Irish jigs (don’t miss the Saint Patrick’s Day concert)
Or listen to live bluegrass music

You’re in for a treat at The Warehouse at FTC.

Regina A. Quick Center for the Arts

The Regina A. Quick Center for the Arts, also known as the Quick, is Fairfield University’s, and the neighborhood’s, cultural hub. This breathtaking location, a hive of creative activity, hosts a variety of entertainment.

A cutting-edge theater, a “black box” theater space, and an art gallery are all available at the center. In these sections, you’ll find engaging performances and other dynamic, frequently experimental exhibits that aim to both inspire and engage their audiences.

Do you want to learn more about the arts? The Quick is a great place to hear Fairfield University professors and other business experts speak:

Politicians
Artists
And humanitarians

Thomas J. Walsh Art Gallery

This art gallery has welcomed tens of thousands of visitors with a one-of-a-kind art experience since 1990 that includes:

Performing
Visual
And literary arts

It is also known as the “White Cube” gallery. Its exhibitions and galleries both display artwork and allow for interactive experiences.

Sacred Heart University Discovery Science Center and Planetarium

Sacred Heart University’s Discovery Science Center and Planetarium is a fascinating place. It’s the place to go in the area to learn about the vastness of space and the celestial bodies.

It’s in Bridgeport, about 15 minutes northeast of Fairfield.

The entire attraction has three stories of interactive exhibits for visitors of all ages to play and learn.

It is an exciting place to visit for massive replicas of our solar system’s planets, spacecraft, space suits, and other related items.

Westport Astronomical Society (WAS)

For nearly 50 years, the Westport Astronomical Society has illuminated the wonders of the night for thousands of visitors.

Their observatory has a 16′ Meade LX200 telescope with an Explore Scientific 102mm f/7 Essential Apochromatic ED Triplet Refractor on top.

And on Wednesday nights between 20:00 and 22:00, if the sky is clear, you are welcome to take a look through it. It’s one of the more unique date night ideas in CT, in case you’re looking for one.

The massive 25′ Obsession telescope is brought out onto the lawn on occasion.

This is the largest telescope available to the general public in Connecticut. And it’s right across the town line from Fairfield.

Hotels, Inns, and Places to Stay in Fairfield, CT

The town of Fairfield, CT, is only a 30-minute drive from our Greenwich, CT, bed and breakfast. With no traffic. So it makes a lovely CT day trip. If you’d rather spend more than a few hours exploring town, there are several places to stay, based on your preferences.

Hotels in Fairfield, Connecticut

The Delamar Southport is a luxury boutique hotel in the Southport area with 44 guest rooms and suites, a spa, and Artisan, a fine dining restaurant. It welcomes dogs and is housed in a historic 1890s mansion.

The Circle Hotel Fairfield is a coastal-inspired boutique hotel with 80 newly renovated rooms, a fitness center, a business center, and an outdoor pool. The hotel is close to Fairfield Beach and Jennings Beach, making it a good pick for beach hotels.

The Hi-Ho Motel is a budget-friendly, stylish motel with rates starting around $100 per night. It is housed in the same building as the popular Fairfield restaurant Barcelona, which serves Spanish cuisine and cocktails.

Dune is a new addition to the list of beach hotels in the area, replacing the Fairfield Beach Inn. It combines style and affordability near Fairfield Beach.

Bed and breakfasts near Fairfield, CT

Apparently, bed and breakfasts have lost their cachet in Fairfield. Even the former Inn at Fairfield Beach doesn’t want that moniker.

So, you’ll have to head to nearby towns if you’d prefer a bed and breakfast. Nearby options are:

Stanton House Inn in Greenwich, CT

West Lane Inn in the town of Ridgefield, Connecticut

Evergreen Bed & Breakfast in the town of Southbury, CT

The Roger Sherman Inn in the town of New Canaan, Connecticut

Directions to Fairfield, CT

Fairfield is an easy drive from New York City, Westchester County, Boston, or anywhere else in New England. Getting here is easy via I-95 and the Merritt Parkway.

Fairfield has three Metro North New Haven line stations, which provide rail connections to New York’s Grand Central Terminal. Amtrak stops at the train stations in nearby Bridgeport and Stamford.

Keeping exploring more things to do in Fairfield County, CT

Fairfield, Connecticut, is a delightful town.