Blake Walsh

15 Best Things to Do in Fairfield County, CT

  • Published 2023/05/28

Fairfield County is a diverse region in Connecticut that bursts with history and culture.

Located southwest of the state, it is bounded by the New York state to the west, the Long Island Sound to the south, and the Housatonic River to the east.

Fairfield County is home to over 900,000 people as of the 2021 census.

Boasting sophistication, the county offers visitors plenty of opportunities for recreation.

It has well-known cultural centers, unique businesses, premier restaurants, and historic sites.

Its proximity to New York City also makes it an attractive place to investors, potential residents, and travelers who want to experience something new without going too far.

From outdoor adventures to state-of-the-art facilities, Fairfield County has it all.

Any kind of traveler will surely find something to enjoy when they visit this place.

Before planning a trip, make sure to check out this list of the best things to do in Fairfield County, Connecticut!

See a Show at Westport Country Playhouse

Entrance to the Westport Country Playhouse

M. Vinuesa /

If you’re a lover of theater, you can’t miss out on the Tony award-winning Westport Country Playhouse.

It is located at 25 Powers Court in the town of Westport.

The professional theater is run by a non-profit group that produces shows from actors, playwrights, directors, and designers of all backgrounds.

The establishment was originally built in 1835 as a manufacturing facility and was later turned into a cider mill.

In 1931, the space was turned into a theater, specifically for Broadway transfer tryouts.

By the end of the 20th century, it had become an established summer stock theater until it was finally renovated and opened again in 2005.

Today, the Westport Country Playhouse serves as a venue for performances, concerts, company meetings, presentations, and lectures, among others.

Be sure to check the scheduled productions and book your seats in advance!

Shop For Unique Items at Estate Treasures

Estate Treasures is one of the best-known consignment shops in the area.

You may find it at 1381 East Putnam Avenue in the neighborhood of Old Greenwich.

It has been offering the community with one-of-a-kind items for over 40 years now.

While here, be sure to browse the collection of curated furniture, jewelry, and accessories, among others!

If you want to find a gem that can also be a souvenir from your trip to Fairfield County, then you should give Estate Treasures a chance!

Book a Tour at The Glass House

Outside view of The Glass House

Ritu Manoj Jethani /

The Glass House is a remarkable structure that exemplifies modern architecture and landscape.

It is situated at 199 Elm Street in the town of New Canaan.

Operated by the National Trust for Historic Preservation, the 49-acre landscape is home to the mid century modern Glass House built by the architect Philip Johnson from 1949 to 1995.

Landscape of the The Glass House

Ritu Manoj Jethani /

Fourteen other structures may also be found within the grounds, including follies and outdoor sculptures.

In addition, the place features a collection of 20th century artworks, temporary exhibitions and online programs.

Be sure to book a tour in advance to fully enjoy the beautiful and historic site of The Glass House.

Exhibits at The Glass House

Ritu Manoj Jethani /

Pick Up Some World-Class Treats at Bridgewater Chocolate

Bridgewater Chocolate offers gourmet and handmade chocolate perfect for gift-giving.

The store is located at 559 Federal Road in the town of Brookfield.

Since it was established in 1955, the chocolate factory and shop has been serving the community with elevated American chocolate.

It boasts bold flavor combinations and generous sizes of chocolate that are worth every cent.

You may even pick a personalized box of chocolates!

If you’re looking for the perfect give to take home from your trip, you should drop by Bridgewater Chocolate and pick from its wide selection of decadent chocolates!

Have an Outdoor Adventure at Blue Spruce Farm

Try horseback riding while surrounded by picturesque nature at Blue Spruce Farm.

You may reach it at 626 Wheeler Road in the city of Monroe.

The farm is a quaint facility that offers riding experiences against a rural backdrop.

Among the activities you may avail here are horseback riding lessons, trail rides, therapeutic riding, and hay rides, among others.

The farm also hosts summer camps for children and holds group events like team building or birthday parties.

Regardless of your skill level, you’re sure to have an amazing experience at Blue Spruce Farm.

Meet the Animals of The Maritime Aquarium at Norwalk

Trainers feeding the sea lion at The Maritime Aquarium at Norwalk

Ritu Manoj Jethani /

If you want to be fascinated by the aquatic creatures of the world, visit The Maritime Aquarium at Norwalk.

You may find it at 10 North Water Street in the city of Norwalk.

The aquarium has 75 live exhibits of more than 7,000 animals, including various sharks, sea turtles, harbor seals, stingrays, mollusks, and so much more!

Seal at The Maritime Aquarium at Norwalk

James Kirkikis /

Aside from aquatic animals, the place is also home to fun animals such as meerkats and tamarins.

The Maritime Aquarium will give visitors a peek into the Long Island Sound, an exceptional ecosystem in the region, starting with freshwater river, the salt marsh, and deeper into the ocean.

You may also book seats to try its very own 4D theater and experience underwater life through the screens!

Display at The Maritime Aquarium at Norwalk

Ritu Manoj Jethani /

Learn About Birds at the Connecticut Audubon Society Birdcraft Museum & Sanctuary

Discover the history of birds when you tour the Connecticut Audubon Society Birdcraft Museum & Sanctuary.

It is located at 314 Unquowa Road in the town of Fairfield.

The museum and sanctuary is designated as a National Historic Landmark, so you can’t miss it when you visit the county.

While here, you may learn about natural history, specifically of birds, through the dioramas, exhibits, and guided tours.

Adjacent to the museum is a six-acre sanctuary with trails, which is a part of the Connecticut Women’s Heritage Trail.

The society that operates the establishment also offers educational programs for all ages, so feel free to inquire about this if you want to broaden your knowledge on animals.

If you’re looking to explore wildlife and history while going on an adventure, you should visit the Connecticut Audubon Society Birdcraft Museum & Sanctuary.

Enrich your Cultural Life at The Palace Theatre

Exterior view of The Palace Theatre

John9474, CC BY-SA 4.0, via Wikimedia Commons

Watch a live performance and see local talents when you go to The Palace Theatre.

You may find it at 61 Atlantic Street in the city of Stamford.

The 1,580-seat theater was designed by architect Thomas Lamb as a vaudeville house.

It originally opened in 1927 and was commended as “Connecticut’s Most Magnificent.”

In 1983, it was restored and reopened as a venue for opera, live theater, dance, concerts, and other performances.

Art exhibitions are also held at a gallery within the establishment.

You may book a tour to explore the theater, dressing rooms, lobby spaces, as well as the hidden backstage murals or buy tickets to see some of the most-awaited performances at The Palace Theatre!

Go Fishing with Stamford Fishing Charters

Stamford Fishing Charters offers an unforgettable fishing experience at the Long Island Sound.

You may find it at Harbor Drive 290 in the city of Stamford.

Here you may book a schedule with an experienced captain who will assist you in angling and take you to exclusive spots that not a lot of people know about.

Onboard the boat are amenities that will make your experience convenient, including a GPS unit, a fish finder device, and a wheelchair ramp.

When you book with Stamford Fishing Charters, tools like the rods, reels, and tackle as well as fishing licenses are already included so you won’t have to worry about anything.

Additionally, your catch may also be cleaned by the crew after fishing!

Add Stamford Fishing Charters to your radar if you wanna explore the coastal area of Fairfield County.

Celebrate Art and Science at Bruce Museum

Native American artifacts displayed at Bruce Museum

Jllm06, CC BY-SA 4.0, via Wikimedia Commons

Bruce Museum is a must-visit for art and science lovers.

It is located at 1 Museum Drive in the town of Greenwich.

The museum features galleries and immersive experiences on culture, art, and natural science.

Some of the permanent galleries you may find here display extraordinary minerals.

In addition, Bruce Museum also conducts educational programs on various topics, so those who want to expand their mind should definitely try to participate.

Add Bruce Museum to your list of cultural and historical stops when you’re in the area!

Taste Local Craft Beer at Charter Oak Brewing Company

If you’re a beer lover, you should taste locally made beer at Charter Oak Brewing Company.

It is located at 39B Shelter Rock Road in the city of Danbury.

It has a brewing system with 20 barrels and a taproom with ten rotating draft lines.

The brewery’s taproom offers a selection of craft beers that are all handcrafted and made in small batches.

Among the varieties you may choose from are pale ales, brown sours, lagers, and other seasonal robust beers.

If you’re interested in the beer-making process, you may even request a tour of the facility!

Charter Oak Brewing Company is also a great place for gathering with friends and spending some quality time over drinks and snacks.

Experience the Keeler Tavern Museum

Exterior view of the Keeler Tavern Museum

Ritu Manoj Jethani /

For a different kind of museum experience, visit the Keeler Tavern Museum.

The living museum is situated at 132 Main Street in the town of Ridgefield.

It is listed on the National Register of Historic Places and provides a glimpse of the locality’s past.

When you tour the museum, you will be guided by a docent dressed in a Colonial costume, giving you an immersive experience of the place.

Interior view of the Keeler Tavern Museum

Ritu Manoj Jethani /

Here you may learn all about the history of Keeler Tavern, including its residents and the important people who once visited it.

After touring the Keeler Tavern Museum, you may also stroll the seasonal gardens within the grounds.

Chandelier at Keeler Tavern Museum

Ritu Manoj Jethani /

Explore the Great Outdoors at Webb Mountain Discovery Zone

Explore and enjoy nature when you visit Webb Mountain Discovery Zone.

You may access it at 71 Webb Circle in the city of Monroe.

The outdoor learning center is situated on 171 acres and about four miles of trails.

It offers educational programs related to nature, science, and history, perfect for students and families.

You may get hands-on experiences through activities such as scavenger hunts.

While here, you may encounter all kinds of wildlife, Native American sites, and Colonial quarries.

If you want to learn while spending some time outdoors, you should visit Webb Mountain Discovery Zone.

Meet Animals at Connecticut’s Beardsley Zoo

Entrance to the Beardsley Zoo

Sage Ross, CC BY-SA 3.0, via Wikimedia Commons

Connecticut’s Beardsley Zoo is the only zoo in the state.

It is situated at 1875 Noble Avenue in the municipality of Bridgeport.

The zoo features over 300 animals, mostly North and South American animals, including some endangered species.

Tiger at the Beardsley Zoo

Sage Ross, CC BY-SA 3.0, via Wikimedia Commons

You may find here a tropical rainforest birds aviary, a farmyard, a carousel, and a cafe.

Some of the threatened species you may learn about and see here are the Siberian tiger, ocelot, Andean condor, red wolf, and golden lion tamarin.

Feel free to check out the concessions and the gift shop available here at Connecticut’s Beardsley Zoo.

Little red fox at Beardsley Zoo

Sage Ross, CC BY-SA 3.0, via Wikimedia Commons

Try Connecticut Wine at Aquila’s Nest Vineyards

Visit Aquila’s Nest Vineyards if you want to know what Connecticut wine is all about.

It is located at 56 Pole Bridge Road in Newtown.

The 10-acre vineyard of the 40-acre farm grows several grape varieties, most of which are hybrid varieties.

Some of the grape varietals available here are Cabernet Franc, Marquette, Baco Noir, Riesling, and Valvin Muscat, among others.

Aquila’s Nest Vineyards offers different wine tasting experiences that you may try from different places within the grounds—from fire pit circles and outdoor seating to indoor spaces and the fairy gazebo.

While here, you may also chance upon some events including live music and psychic readings!

Final Thoughts

Fairfield County is the perfect place to visit for cultural and historical explorations.

If you want to travel while learning and enjoying the arts, then you should give this county a chance.

In addition, nature excursions and coastal activities are also accessible here.

You won’t run out of adventures to try when you visit Fairfield County.

For future reference, you should bookmark this list of the best things to do in Fairfield County, Connecticut!

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