Explore Fairfield County :: Monroe


“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.Monroe

The town of Monroe is located in the eastern region of Fairfield County in southern Connecticut. A family-oriented community, Monroe offers a landscape full of beautiful parks and farms. It is a mecca for those who enjoy the quieter side of Fairfield County. With a population of approximately 18,500, this quaint little New England town ranks #19 on Niche’s list for the Best School Districts in Connecticut.

Monroe has just three elementary schools: Monroe El, Stepney, and Fawn Hollow (Grades, K-5). It has one middle school: Jockey Hollow (Grades 6-8), an alternate STEM program housed at Masuk High School, and one high school: Masuk (Grades 9 – 12). Here are the top 10 things that I love about this town.

1. Wolfe Park

With sprawling sports fields, tennis courts, picnic pavilions, playgrounds, and a pool, Monroe residents and neighboring towns love hanging out at Wolfe Park. The town did a community build in 2022, and now Wolfe Park has a gorgeous new playground! This beautiful spot offers a non-resident parking lot, just a short distance from the main one. Families can join the pool for a moderate fee in the summer and take in live theater or music, thanks to the Arts in the Park Summer series.

2. Great Hollow Lake

This may be my favorite place to be in Monroe. I love to trail run here! Whether you want to run or walk around the lake, kayak or paddleboard on the lake, have a play date on the beach/playground, or go trout fishing, Great Hollow is fun for every age.

The kiddos can’t wait for the character dinners most Wednesday evenings in the summer, where Scooby Doo, Mickey Mouse, and other fun characters are ready to meet and greet your little ones. Paddle boats, face painting, and children’s entertainment are also a part of these Wednesday summer nights.

3. Festivals on the Green

No matter the season, there is always something special to look forward to at the town green. In the fall, we celebrate apples. In the spring, we love our strawberries. Monroe is probably best known for its annual Apple and Strawberry Festivals, which offer craft vendors, bouncy houses, children’s games, and tasty goodies embracing the fruit theme. In the winter, Santa arrives on a firetruck at the Green’s gazebo for our annual tree lighting ceremony.

4. Edith Wheeler Memorial Library

This library is a wonderful town resource. Well-stocked and with a knowledgeable staff, Edith Wheeler is a spacious library that has something for everyone. Moms of young children take advantage of their play area and weekly programs. Teens love to hang in their cool lounge area upstairs. Special programs like reading to service dogs, the annual summer reading initiative, and literary-centered activities can’t help but get your children wild about reading.

5. Mom and Pop Shops

Yes, Monroe has more than just pharmacies, pizza places, and nail salons! Quaint mom-and-pop stores and eateries line the main roads of Rt. 25 and Rt. 111. A favorite book shop is Turning the Page. Some favorites for food and drink are The Last Drop Coffee Shop, serving up delicious lattes, Terra Cafe and Soup Thyme offer savory lunches and bites, and Bill’s Drive-In offers a quick lunch.

6. The Farmers’ Market

Every Friday from June through October, Monroe Farmers’ Market is bustling in front of our town hall from 3 – 6 p.m. Live entertainment, homemade Italian ice, and wood-fired pizza are just a few of the special surprises among the fresh produce and products at this great market. Our favorite Friday is the Annual Back to School Bash; imagine a live bunny pen as just one of many fun activities for the children to enjoy!

7. Webb Mountain

Monroe has no shortage of woods and wildlife, including some great hiking at Webb Mountain. A place to get lost in nature and have some peace and quiet.

8. Farms Galore

Agriculture was once a major part of Monroe’s history and is still a part of its current lifestyle. Zenkos, Pondview, Silver Lining Stables, and Blue Spruce are just a few of the farms that make up Monroe’s landscape. Whether it be horseback riding, fresh vegetables, or Christmas trees, these farms are an important part of our community. Another staple is Benedict’s Home & Garden store, which sells agriculture and garden supplies and is one of Monroe’s best-kept secrets for autumn hayrides and fun activities.

9. Memorial Day Parade 

The Sunday before Memorial Day, parade marchers line up on Elm Street, ready to participate in the traditional Memorial Day Parade. Schools, sports teams, Scouts, local businesses, tractors, bands, and organizations are all active participants in this annual parade. Parade-goers sit along Rt. 111 from Elm Street to the town green, hoping to spot a friend or family member and catch some candy!

10. Housatonic Bike Trail

The Monroe Housatonic Bike Trail is the last leg of the Pequonnock Valley Greenway. It is part of a system of bike trails stretching from Seaside Park in Bridgeport to Newtown. The Housatonic trail begins at Great Hollow Lake Park and primarily runs along Pepper Street. Not just bike riders can be seen enjoying this peaceful stretch of dog-friendly trail.

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

Please read all the Explore Fairfield County Series posts by clicking here.


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