Explore Fairfield County :: Sherman


“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.Sherman

Sherman, CT is the northernmost town in Fairfield County, CT. It also has the smallest population which hovered at 3,581 on the 2010 census. Established in 1802, Sherman, CT was named after Roger Sherman, famous for being the only person who signed all four founding documents of the United States of America. Formally Algonquian territory, 18th century colonial settlers purchased the land, along with New Fairfield, CT, in 1729. It’s land includes parts of the Appalachian Trail, Candlewood Lake, Squantz Pond, and the Sherman Center.

Sherman is the only town in Fairfield County to have the 860 area code. It has been named “Best Small Town in Connecticut” three times by Connecticut Magazine. 

1. The American Pie Company

If just passing through or staying in Sherman, CT, a stop at The American Pie Company is a must. Around since 1993, the American Pie Company is known for more than just their pies. They provide home-style meals and baked goods from scratch. The portions are relatively large and adequately priced. While the baked goods include muffins, cookies, and tarts, the pies are their specialty. They are hand-rolled and filled with a variety of items from apple to chocolate cream to strawberry rhubarb. Yum!

2. White Silo Farm & Winery

White Silo is a family-owned farm and winery located in Sherman, CT since 2000. They offer a wide variety of wine for tasting and purchase. For $8.00 you can sample four of their wines including Rhubarb, Blackberry, and Raspberry in a souvenir glass. They offer cheese platters and gourmet lunches for purchase that you can enjoy while sitting outside at their terrace gardens taking in the gorgeous views.

In addition, White Silo has rotating artwork for viewing and purchase from local artists. They also host many festivals during the year including their Hot Chocolate Festival, Blackberry Festival, Raspberry Festival, Beet Festival, and Quince Pear Festival. Provided during these festivals are dishes made with their farm-grown produce for purchase, live music and winery tours.


3. Happy Acres Farm

Located on Taber Road in Sherman, CT, Happy Acres Farm offers grass-fed beef, eggs, and organic vegetables for purchase. Their farm stand is open every Sunday from 11:00 a.m. – 2:00 p.m. They have several fun family-friendly activities during this time. Most recently, they offered a Medicinal & Edible Plant Walk with a local herbalist and a Drum Circle. Throughout the year there are several educational programs. Farm tours are available and need to be scheduled as they are by appointment only. 

4. Deer Pond Farm

Obtained by The Connecticut Audubon Society in 2017 from the estate of Kathryn D. Wriston, Deer Pond Farm is over 835 acres of forest, meadows, and wetlands. The property lies in both Sherman, CT and Pawling, NY. Deer Pond Farm has 20 miles of trails. As of July 7th, 2018, Sherman’s 10 miles will be open to the public. Deer Pond Farm provides several guided programs including Ecology Walks with their conservation biologist, Jim Arrigioni, and Bird Walks with the senior director of science and conservation for The Connecticut Audubon Society, Miley Bull. These walks are roughly 1.5 miles and moderate in terrain. They are free for Audubon Society members and $5.00 for non-members. 

5. Chicken Rock

A daredevil tourist attraction located in the middle of Candlewood Lake in Sherman, CT, Chicken Rock is a large rock that is used by many as a jumping-off point into the lake at the tip of Green Island. Standing roughly 25 feet above the water, the rock is accessible only by boat. Many cruise their boats over to the rock, climb out and walk the short trail to the top and then proceed to jump off. There is also a rope swing for access to the water. Proceed with caution though as a few accidents have occurred through the years. Chicken Rock is even the topic of several ghost stories.

6. Candlewood Lake

Approved for creation in 1926 by Connecticut Light & Power, Candlewood Lake is the first large-scale operation of pumped facilities in the United States. This lake is bordered by not only Sherman but also by Brookfield, Danbury, New Fairfield, and New Milford. Not only used by utility companies, but Candlewood Lake is also a popular tourist destination for swimming, fishing, boating, and golfing. 

7. Herrick Trail Preserve

Herrick Trail Preserve is part of the Naromi Land Trust in Sherman, CT.  It’s 2.35 miles connects to the allusive Appalachian Trail. There are two overlooks. The first, Housatonic Overlook, provides a spectacular view of the Housatonic River which winds north through gentle hills. Amy’s Overlook, the second, provides views of Mountain Laurel and a chance to see turkeys and hear the melody of the birds singing.

8. Irene’s Woods Preserve

Also part of the Naromi Land Trust in Sherman, CT, Irene’s Woods Preserve sits close to Sherman’s border with New Milford, CT. Looping Flat Rock, a Vernal Pool and Split Rock, Irene’s Woods Preserve offers rough access to Towner Hill Preserve. You can also access this 53 acre preserve through White Silo Farm & Winery. Irene’s offers not only hiking trails but is a Wildlife Sanctuary too.

9. The Sherman Players / The Sherman Playhouse

Created by the Evans family in the early 20th Century, the Sherman Playhouse came about from Mrs. Evans desire to continue with her love of theater after moving to Sherman from Staten Island, NY. The playhouse was a dilapidated church prior to it’s “resurrection.” The Sherman Players were incorporated in 1949. Since this time the Players have been putting on an array of plays, workshops, films, and concerts. Mrs. Evans daughter, Betsy Scholze, has remained active in The Sherman Players by serving as President, Treasurer, actress, director and set designer over the last 50 years. Productions for the 2018 season include Other Desert Cities, The Underpants and A Christmas Story. Ticket prices run $24 – $30 a person and $12 – $15 for students.

10. The Sherman Historical Society

Created 39 years ago, The Sherman Historical Society aims to educate residents and visitors on the history of Sherman, CT from its time as Native American land to present day. The Historical Society includes the Northrop House Museum. The Northrup family was a prominent family in Sherman with David Sr. becoming the first town clerk in 1802. The property was once a working farm but is now home to a permanent exhibit about Roger Sherman and several rotating exhibits. Access to the Mallory Trail, a scenic walking trail, is located on this property. Tours are by appointment only during the months of May – October. The Historical Society also runs a ‘Hooked on History’ kids summer program for those entering grades 1 – 6 which educates children on what life was like in the early 1900s.  

Have you visited Sherman? 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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