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and the Moms Who Live Here

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 10 things they love about each local area. To read more in this series click here.

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 19,500, this quaint little New England town ranks #1 in Niche’s list for the Safest 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) with 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

Sprawling sports fields, tennis courts, picnic pavilions, playgrounds, and a pool, Monroe residents and neighboring towns alike love hanging  out at Wolfe Park. This beautiful spot offers a non-resident parking lot just a short distance from the main one. In the summer, families can join the pool for a moderate fee as well as take in live theater or music thanks to the Arts in the Park Summer series. A trail to Great Hollow Lake is available for those that like a good hike.

2. Great Hollow Lake

This may be my favorite place to be in Monroe. Whether you want to run or walk around the lake, have a play date on the beach/playground or go trout fishing, Great Hollow is fun for every age. This tranquil spot is often the host for the Race4Chase Triatholon, Autism SpectRUN, and other similar events. 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.


Great Hollow Lake

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 most well known for their annual Apple and Strawberry Festivals which offer craft vendors, bouncy houses, children’s games, and tasty goodies embracing the fruit theme. In the summer, families in town love to head over to Fireman’s field (next to the green) for their annual July carnival. In the winter, Santa arrives on a firetruck at the green’s gazebo for our annual tree lighting ceremony. 


All things strawberry at the annual Strawberry Festival in June.

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: children, teens, and adults. 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.


Side-by-side Collection Displays at the library for these two!

5. Mom and Pop Shops

Yes, Monroe has more than just pharmacies and nail salons! Quaint mom and pop stores and eateries line the main roads of Rt. 25 and Rt. 111. Some favorite stores include, Linda’s Story Time for both adult and children books and The Mason Jar for women’s clothing, accessories, and locally made goods. For food and drink: The Last Drop Coffee Shop serves up delicious lattes, Veracious Brewery for freshly brewed beer, Gaetano’s Deli and Soup Thyme for a savory lunch, and Bill’s Drive-In if you need a quick bite to eat (that’s not from the golden arches down the street). 

6. The Farmers’ Market

Every Friday during the months of 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. Two Planks Theater Company

Monroe is lucky enough to have their very own theater company to inspire and educate artists while showcasing the performing arts. They produce three powerful productions throughout the year. During the summer, both juniors and teens can take part in their Summer Theater Workshop which incorporates master classes, music, dance, and voice. During these workshops, students also rehearse for a full production showcased under the lights in Wolfe Park along with a final adult performance as a part of the Arts in the Park Summer Series. 


Photo courtesy of Two Planks Theater Company

8. Farms Galore

Agriculture was once a major part of Monroe’s history and is still much 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 also is one of the Monroe’s best kept secrets for autumn hay rides and fun activities.


9. Memorial Day Parade 

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


Memorial Day Parade ready!

10. Housatonic Bike Trail

The Monroe Housatonic 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?

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


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