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, including 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.

Sherman, CT, is the northernmost town in Fairfield County. It also has the smallest population, which hovered at 3,527 on the 2020 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. Its land includes parts of the Appalachian Trail, Candlewood Lake, Squantz Pond, and the Sherman Center.

Sherman is the only town in Fairfield County with the 860 area code. Connecticut Magazine has named it “Best Small Town in Connecticut” three times.

I contacted one of my good friends in Sherman to get the inside scoop on all the must-visit places. On a gorgeous late spring afternoon, I drove up to Sherman to visit everything for myself.

1. The American Pie Company

If just passing through or staying in Sherman, CT, a stop at The American Pie Company is a must. Since 1993, the American Pie Company has been known for more than just its pies. They provide homestyle meals and baked goods from scratch and have a full on-site restaurant. While the baked goods include muffins, doughnuts, cookies, and tarts, the pies are their specialty. They are hand-rolled and filled with various items, from apple to chocolate cream to strawberry rhubarb. I asked them what their best-sellers are, and they said the homemade frozen chicken pot pies and their peach raspberry pie. Pie is my favorite food, so I had to get one of each. Yum!

2. Sacred Ground Coffee Roasters 

Like most moms I know, coffee is life for me many days. Even though I already had coffee this morning, I still headed over to Sacred Grounds Coffee Roasters to check out their menu. Sacred Grounds Coffee Roasters is a USDA-Certified Organic and Fair Trade Certified wholesale and retail small-batch roastery. They pride themselves on being low impact on the environment and pricing their coffees so that Fair Trade and Organic Coffee can be accessible for all. Their coffee does not disappoint. They offer a variety of ground and whole bean coffee for sale, as well as cups to go. As well as a coffee, I picked up a large double chocolate biscotti made locally by White Silo Farm & Winery.

3. White Silo Farm & Winery

White Silo has been a family-owned farm and winery located in Sherman, CT, since 2000. They offer a wide variety of wines for tasting and purchase. For $14/pp, patrons can sample five of their wines, including Rhubarb, Blackberry, and Raspberry, in a souvenir glass. Bottles are also available for purchase on-site. They offer cheese platters and gourmet lunches for purchase that you can enjoy while sitting outside in 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.

4. Sherman Library

The Sherman Library officially opened in the Town Center in 1926 with a membership of just 46 families. By the 1950s, the library had grown to offer a collection of nearly 5000 books. Now the home to over 25,000 books, audiobooks, films, and other materials, the Sherman Library provides over 320 free programs, exhibits, story hours, book discussions, concerts, and collaborative town events each year. They offer various programs free of charge for children of all ages, both during the day for younger children and after-school programs for the school-aged set. Visit their website for current offerings.

5. Candlewood Lake

Just a quick drive (or walk) down the street from the library is the cutest little beach and park set right on the picturesque Candlewood Lake. Candlewood Lake borders several towns in Fairfield and Litchfield counties, including Danbury, New Fairfield, and Sherman. At 8.4 square miles, it is the largest lake in Connecticut. Bring a picnic lunch, enjoy the lake, and park with your family, or take a solo walk along its beautiful shore.

6. 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 her love of theater after moving to Sherman from Staten Island, NY. The playhouse was a dilapidated church prior to its “resurrection.” The Sherman Players were incorporated in 1949. Since then, the Players have been putting on various 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. Ticket prices run $24-$30 per person for adults and $12-$15 per person for students. Masks are now optional but still recommended. Please visit their website for more information.

7. The Sherman Historical Society

Since 1975, the Sherman Historical Society has aimed to educate residents and visitors on the history of Sherman, CT, from its time as Native American land to the present day. The Historical Society includes the Northrup House Museum. The Northrup family was prominent 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. They offer tours from May through October. The Old Store Gift Shop and Museum, located across the street, has historical pictures, goods for sale, and unique gifts for all ages.

8. The Connecticut Audubon Society – Deer Pond Farm Sanctuary

Obtained by The Connecticut Audubon Society in 2017 from the estate of Kathryn D. Wriston, the Deer Pond Farm Sanctuary covers 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 and offers small-group outdoor programming. Members receive discounts on these programs, and children who are members can attend for free. The Deer Pond Farm Sanctuary is open daily from dawn to dusk. Trails are open to the public and are free to all.

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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Charity is a newly-single mom of three with a son born in 2012 and identical twin daughters born in 2017. She lives in Monroe and has been writing for Fairfield County Mom since 2019. Charity is a full-time speech-language pathologist, working with patients all across the lifespan. She is also an intuitive medium. In her life before children, Charity was a professional stage manager, working in theatres throughout Fairfield County. Charity is passionate about her family, career, ballet (which she began at 39 years old!), musical theatre, and her amazingly-supportive friends as she begins a new chapter in her life. She firmly believes that you are never too old to stay stuck in a situation that is causing you pain. You can follow her on Instagram at @charityferris.


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