Visit Sherman, CT | Travel Guide & Things to Do

Sherman Connecticut in Fall October Color

Sherman is a picturesque town in the Litchfield Hills of Connecticut. Although it is the smallest town in Fairfield County, it has previously been nominated as the "Best Small Town in Connecticut." It offers a quiet, rural escape with access to Candlewood Lake, historic sites, and stunning seasonal foliage.

Local Businesses & Organizations

American Pie Company

A popular, long-standing bakery and restaurant established in 1993. Renowned for its "from scratch" homestyle comfort food and wide variety of daily baked goods, it has served as a cozy, rural cornerstone of the Sherman community for over 30 years.

Restaurant & Dining: Serving breakfast, lunch, and dinner. Signature dishes include chicken pot pie, meatloaf, and pot roast. Indoor and outdoor seating available.
Retail Bakery: Everything is baked on-premises daily, including hand-rolled pie dough, cookies, tarts, muffins, and artisan breads.
Atmosphere: Features a welcoming, rustic environment located at 29 Route 37 S.
Services: Offers convenient takeout and curbside pickup options alongside traditional table service.
A destination for traditional New England comfort food and handmade pastries.

Deer Pond Farm

An 850-acre nature sanctuary managed by the Connecticut Audubon Society. Located on an elevated site near the New York border, it protects a diverse ecosystem of forests, meadows, and wetlands, serving as a vital habitat for over 150 bird species.

Recreation & Trails: Features over 15 miles of well-marked trails for hiking, birding, running, and snowshoeing, with elevations reaching 1,200 feet for scenic views.
Access & Hours: Open to the public daily from dawn to dusk. Note: No dogs are permitted on the property to protect the natural habitat.
Programs: Offers a seasonal pollinator garden and a variety of guided, nature-focused conservation programs and activities.
Mission: Focused on conservation and providing natural habitat; the property does not feature developed park amenities like playgrounds or ball fields.
A premier Litchfield Hills destination for birders and nature enthusiasts seeking quiet reflection.

Holy Trinity Chapel

A Catholic chapel and worship site for St. Edward the Confessor Parish (New Fairfield). Following the replacement of the original structure due to age, a newly constructed "quaint and tasteful" chapel was completed in late 2025 to serve the Sherman community.

Location & Diocese: 15 Route 39 North, Sherman, CT. Operated as part of the Diocese of Bridgeport.
Mass Schedule: Typically holds a weekly Sunday Mass at 10 AM.
Features: The 2025 design features a striking 25-foot stained glass window and specialized lighting architecture.
Dedication: Formally dedicated on December 21, 2025, by Bishop Frank Caggiano and Rev. Robert Wolfe.
A modern spiritual landmark preserving a long-standing presence in the Litchfield Hills.

The Daily Market

A locally owned country grocery store and community hub situated in the center of Sherman. Replacing the former Sherman IGA, the market focuses on curated, farm-to-table quality products, including local, sustainable, organic, and GMO-free foods alongside traditional staples.

Ownership: Owned by Chefs Rich and Cassie Parente (formerly of Clock Tower Grill), bringing high-level culinary expertise to the local grocery scene.
Offerings: Fresh produce, deli meats and cheeses, coffee, baked goods, prepared take-away items, and unique specialty products.
Atmosphere: Positioned as a neighborhood "gathering space" and community cornerstone prioritizing a personalized shopping experience.
Services: Online ordering and in-store pick-up are available for convenience.
Recognized for a deep commitment to sustainability and local community engagement.

White Silo Farm & Winery

A family-owned boutique winery specializing in small-batch wines crafted from farm-grown fruit. Situated on 17 scenic acres in the Litchfield Hills, the winery centers around a beautifully renovated 18th-century dairy barn that serves as a tasting room and event space.

Winery & Dining: Wine flights (including signature Raspberry), cheese platters, baked goods, and gourmet picnic lunch boxes.
Seasonality: Tasting room open late April–December; Pick-Your-Own raspberries available September and October.
Events: Hosts seasonal festivals (Hot Chocolate, Asparagus, Rhubarb), Valentine’s dinners, and specialized food weekends.
Property & Private Events: Dog-friendly atmosphere with gardens and outdoor seating. Venue available for weddings and parties (70-150 guests).
Known for its relaxed, scenic environment in the Connecticut countryside.

Sacred Grounds Coffee Roasters

A USDA Certified Organic and Fair Trade small-batch roastery and café. Functioning as a community hub, it focuses on ethically sourced, high-quality specialty coffee in a welcoming atmosphere for on-site service or takeout.

Offerings: Single-origin and signature blends, teas, hot chocolate, and nitro cold brew.
Values: Sustainability, ethical sourcing, and direct partnerships with growers.
Availability: Roasted coffee is also available at regional Caraluzzi's markets.

Sherman Library

A private association library serving as a comprehensive free public resource for the Sherman community. Located at the town center, it acts as a gateway to information, education, and recreation through its extensive collections and diverse programming.

Location & Resources: Situated at 1 Sherman Center. The collection features over 25,000 items, including books, audiobooks, films, and various media materials.
Programs: Hosts over 320 free events annually, including children's story hours, art exhibits, concerts, and community-focused workshops.
Mission: Dedicated to providing free and equal access to knowledge and community engagement for all residents and visitors.
Funding: Operated through a combination of private donations, memberships, and annual grants from the Town of Sherman.
A vital intellectual and social hub located in the heart of the community.

The Sherman Playhouse

A premier non-profit community theater providing high-quality, affordable performing arts since 1926. Operated by the Sherman Players, the playhouse serves as a cultural hub for the Litchfield Hills, showcasing local professional and volunteer talent.

Venue: Located at 5 Route 39 North in a renovated 19th-century church, featuring unique original pews for audience seating.
Programming: Hosts a diverse annual calendar of musicals, classic dramas, and modern plays.
Mission: Fostering community through live theater, including acting, directing, and technical stage design.
Organization: A 501(c)(3) non-profit supported by ticket sales and community donations.
A historic cornerstone of the Sherman arts scene for nearly a century.

Sherman Chamber Ensemble (SCE)

A 501(c)(3) nonprofit organization established in 1982. SCE brings world-class musicians to the Litchfield Hills, featuring a diverse repertoire of Baroque, classical, and jazz-inspired programs, alongside community outreach and children's concerts.

Leadership: Notable musicians including flutist Susan Rotholz.
Mission: Bringing elite musical performance to local communities in Sherman, Kent, and Washington, CT.

Sherman Historical Society

Dedicated to preserving and promoting the history of Sherman—Fairfield County’s northernmost town, incorporated in 1802 and named after Founding Father Roger Sherman. The society serves as the primary custodian of the town's rural heritage and cultural evolution.

Northrop House Museum: Located at 10 Route 37 East in an 1829 federal-style house. Features exhibits of local artifacts and period furnishings.
Mission: Focused on collecting and interpreting materials that document the town's shift from its agricultural roots to the era of Candlewood Lake.
Operation: The museum is generally open seasonally from May through October.
Retail: Operates "The Old Store" museum gift shop, offering Sherman-themed items and historical books.
A vital resource for understanding the storied past of the Litchfield Hills region.

Explore the unique rural charm of New England's hidden gem.