Explore Fairfield County :: Fairfield


“Explore Fairfield County” is an informational series that provides a glimpse into the wonderful towns and cities in Fairfield County. Fairfield County is diverse in that it includes big cities, small suburbs, beaches, farms, and busy highways. It covers a large geographic area and, because of this, it has a lot to offer families! To help you get the most out of Fairfield County, our contributors have shared the top things they love about each local area. To read more in this series, click here.Fairfield

Established in 1639, the Town of Fairfield is on the eastern side of Fairfield County, along the Gold Coast of Connecticut, on the Long Island Sound. The southern side of town is heaven for those craving a coastal lifestyle, while the northern side of town is full of beautiful trees and green space. There are roughly 62,000 residents in town, and Fairfield has many desirable neighborhoods. There are eleven neighborhood elementary schools, three middle schools, and two high schools. The town is also home to a few parochial schools. Fairfield Prep, Fairfield University, and Sacred Heart University can also be found in this quaint town.Fairfield

1. All the Beaches

There was no question that this belongs at the top of the list. From Penfield Beach on the north side of town to Sasco Hill Beach in Southport, there is no shortage of sandy spots to enjoy the sunshine. For those who enjoy sailing and boating, Jennings Beach also encompasses the South Benson Boat Marina. Penfield Beach offers two waterfront banquet facilities, which are popular locations for weddings and special events.

You can also take swimming and sailing lessons through Fairfield Parks and Rec at certain beach locations, dogs can run around during the off-season, and if you ever need photos taken for a wedding, prom, or holiday cards, these beautiful beaches make the perfect backdrop. The beach area is a very desirable area to live in, especially for its walkability to the downtown shops and restaurants.

2. The Sandcastle Playground and The Sandy Ground

When Sandcastle Playground was constructed, it brought the community together and still does the same thing today. From the castle, complete with a bridge, to the personalized bricks laid along the walkway, there is much to love about this spot. It’s the perfect place to jump on a swing, play Frisbee in the open space, or enjoy dinner on a picnic table.

In addition to Sandcastle Playground, The Sandy Ground is another beloved spot for children and tots! Along with swing sets for the kids, Penfield beach is the site of The Sandy Ground: Where Angels Play Project. This playground was built in memory of Jessica Rekos, one of the twenty-six victims of the shooting at Sandy Hook Elementary. It is an honor to have a special spot in town to celebrate her beautiful life!

Please note that during the beach season, you need a Fairfield Beach sticker to park your car at either of these playgrounds.

3. The Farmer’s Market

This is a new Sunday tradition for our family! The Fairfield Farmer’s Market runs on Sherman Green from June through October. It is filled with fresh produce, special sweets, and many homemade items from over twenty local farms and food producers. And while all the items to purchase are top-notch, the friendly faces make the market special.

There is also a market in Greenfield Hill on Saturdays from 10 a.m. to 1 p.m. at 75 Hillside Road. These seasonal spots are a nice way to spend a weekend morning supporting local businesses!

4. The Public Libraries

Fairfield has two public libraries. The Fairfield Public Library (main branch) offers year-round classes and events for all ages. For example, new moms can enjoy “Baby Rhyme Time” to meet other new mothers. There are also teen and adult programs that run throughout the year as well. The Fairfield Woods Branch is walkable for students who attend Fairfield Woods Middle School, so many students take advantage of this opportunity by walking to the library after school for a quiet space to do homework.

The Pequot Library is located down the road in Southport, so there are even more books to enjoy and activities to participate in!

5. The Sherman Green Concert Series

From Memorial Day to Labor Day each year, people can enjoy live music at the gazebo on Thursday, Saturday, and Sunday. The concerts are a great way to spend your nights during the nice weather.

6. Adorable Shops Galore

There is no shortage of adorable local shops to stop into when it’s time to make a purchase. In the Mood Intimates is the place to buy intimate wear, and The Beehive, Olive My Stuff, The 203, and Vintage Garden are notable favorites!Fairfield

7. Food for Days

From American to Indian, to seafood to vegan options, Fairfield has become one of the hot spots in Connecticut for going out to eat. The best part is many family-friendly joints such as Flipside Burgers, The Little Pub, Centro, Malibu Taco, and Chips. You can also adult with a date night at Bodega, The Sinclair, Fairfield Social, Old Post Tavern, Geronimo Bar and Grill, Artisan, The Chelsea, and Little Goose. There are many, many more places that I could list! There are also many grab-n-go options, such as Playa Bowls, Pronto, and the Pantry. The food choices in Fairfield are endless, and you can’t go wrong at any of them!

8. An Abundance of Family Activities

There are countless fun places to take the family. Whether painting at Hands on Pottery or checking out the turtles and owls at the Audubon Society, there are countless fun places to take the family. There are hiking trails, playgrounds, a sprinkler park, and Lake Mohegan, Penfield, or Jennings beaches. You can always find something to do with the family!

9. Responsible Babysitters

This could be one of the best things that Facebook could be used for! Between two high schools and two universities in town, there is always a rock star student available to look after your children. The University Sitters page on Facebook is insanely helpful. When you are looking for a night out with your significant other or getting together with friends, this page will lead you to wonderful sitters.

10. Entertainment

Live music and theater lovers will find several venues to go to and listen to their favorites. The Fairfield Theatre Company and Fairfield Center Stage are two of the best. We are also lucky to live in a town just a short train ride away from NYC when we are craving all that comes with the entertainment diversity there!

Have you visited Fairfield? Do you live here? What do you love about it?

Read all the posts in our Explore Fairfield County Series by clicking here.


  1. Great read, Caitlin! This is the best place I have ever lived. Thanks for showing everyone why Fairfield is so special!


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