Explore Fairfield County :: Fairfield

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“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 10 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 shoreline of 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 consists of many desirable neighborhoods (Southport, Greenfield Hill, the University Area, Stratfield, the Fairfield Beach Area, and Melville Village, to name a few). 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, Notre Dame High School, along with Fairfield University and Sacred Heart University.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 some 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, 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 it still does the same thing now. From the castle complete with a bridge to the personalized bricks laid along the walkway, there is so 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 such an honor to have a special spot in our town to celebrate her beautiful life!  

Please note that during the beach season, you do 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 the 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, it’s the friendly faces that really make the market special. We love Yalla Organic for their cold-pressed veggie juices and hummus dips, and MuggersMarrow BBQ Sauce for their grilling glazes and marinades!

There is also a market in Greenfield Hill on Saturdays from 10 a.m. to 1 p.m. at 75 Hillside Road. Vendors include Maia yogurt, Beldotti’s baked breads, and Vaszouka’s Farm!

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. Teens can learn and meet new friends at the “Anime Club.” Adult programs include “One-on-One Career Counseling.” The Fairfield Woods Branch is walk-able 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 Town of Fairfield Christmas Tree Lighting

The first Friday in December holds a special tradition in town – the annual Christmas Tree Lighting on the town green. Local choirs sing carols and candy canes are abundant. The best part? Santa and Mrs. Clause come racing into town on a firetruck! The First Church Congregational Holiday Bazaar opens the same night as the lighting and is right across the street so that you can attend two staple holiday events on the same evening!

6. Adorable Shops Galore

There is absolutely 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, No. 299 is a great spot to grab a gift for a friend, and Saltwater has adorable children’s clothing and jewelry. Since reducing, reusing, and recycling has always been important to me, I am a huge advocate for BD Provisions and The Label Exchange. You can save money and save the environment! The Beehive, Olive My Stuff, Swim and Surf, Vintage Garden, Island Outfitters, and Kate and Hale are also notable favorites!


7. Food for Days

From American to Indian, to seafood to vegan options, Fairfield has become one of the hottest spots in Connecticut for going out to eat. The best part is, there are many family-friendly joints such as Flipside Burgers, Plan B, The Little Pub, Centro, Brick and Wood, Local, and Chips. Still, you can also adult with a date night at Bodega, The Sinclair, Malibu Taco, Fairfield Social, Old Post Tavern, Geronimo Bar and Grill, Artisan, Little Goose, Brickwalk Tavern, and Quattro Patzi. I couldn’t even name them all! There are also many grab-n-go options such as Catch a Healthy Habit, Playa Bowls, BGood, and the Pantry.

8. An Abundance of Family Activities

Whether it’s painting at Hands on Pottery or The Studio, or checking out the turtles and owls at the Audubon Society, there are countless fun places to take the family. There are also events held at Giant Steps for free, and in the summertime, there are tons of outdoor activities hosted all over town. There are hiking trails, playgrounds, a sprinkler park, the beach at Lake Mohegan, The Adventure Park at the Discovery Museum (technically located in Bridgeport but great outdoor fun for the family), Gould Manor Park, Owen Fish Park, and Jennings Beach Skate Park.

9. Responsible Babysitters

This. Is. Clutch. 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. What good are all the indulgent evening events in town if you don’t have a trustworthy person to leave your kids with?

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. In the summer, Fairfield Parks and Rec put on their Summer Jam Movie Nights at Jennings Beach sponsored by many local businesses. It’s a must-do with the kids every summer. 

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

Be sure to read all the posts in our Explore Fairfield County Series by clicking here.

Valerie is a leader in the Fairfield Real Estate Market. She specializes in successfully listing and selling properties. She strives to provide her clients with unparalleled excellence in personalized professional service and achieve the goals they desire with innovation, integrity, and compassion. Valerie works with each client to develop the most effective strategy for marketing the property, including integrating the latest print and digital technology and optimizing online exposure. As a Berkshire Hathaway HomeServices Realtor, she has access to the latest technologies to list, sell, and market each home virtually. In her free time, Valerie enjoys volunteering at her childrens’ schools whenever possible. She also loves reading, playing outside with her girls and pets, and dancing to Country music! 


  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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