Sherman, Connecticut Travel Guide – History, Travel, Hotels, and More!

Sherman, Connecticut is a hidden gem nestled in the scenic Housatonic Valley. This charming town, nominated as the best small town in Connecticut, offers a perfect escape from the hustle and bustle of city life. You’ll find yourself surrounded by natural beauty and small-town charm.

Sherman’s location at the northern end of Candlewood Lake, the largest lake in Connecticut, makes it an ideal destination for outdoor enthusiasts and nature lovers. You can enjoy swimming, boating, and fishing during the warmer months. The Connecticut Audubon Society’s Deer Pond Farm offers hiking trails and birdwatching opportunities year-round. As you explore Sherman, you’ll discover its rich history at The Old Store Gift Shop & Museum. For entertainment, catch a show at The Sherman Playhouse.

Sherman 2025 Deals!
Get a discount of 15% to 70% on accommodation in Sherman! Look for deals here:
Sherman Hotels, Apartments, B&Bs

With its peaceful atmosphere and natural beauty, Sherman provides a perfect retreat for your next Connecticut getaway.

How to Get to Sherman

Getting to Sherman, Connecticut is easy by car. You can take I-84 to Danbury, then follow CT-39 through New Fairfield to reach the town center. This route is ideal if you’re coming from the east or west. From New York City, take I-684 North, then Route 22/37 from Brewster. This path leads directly to Sherman’s center.

If you’re traveling from the north, you have two options:

Take Route 7 South
Follow Route 22 South, then take 55/37

Both routes will bring you to Sherman. Public transportation options are limited. The nearest major airports are:

Stewart International Airport
Tweed New Haven Regional Airport
LaGuardia Airport
Bradley International Airport
JFK Airport
Newark International Airport

From these airports, renting a car is your best bet for reaching Sherman. The town’s scenic roads make for a pleasant drive, allowing you to enjoy Connecticut’s beautiful landscapes along the way.

What to See in Sherman

Sherman, nestled in Fairfield County, offers charming sights and natural beauty. You’ll find plenty to explore in this quaint town. Candlewood Lake is a must-visit attraction. It’s the largest lake in Connecticut and perfect for swimming, boating, and fishing. The lake’s shores burst with bright reds, oranges, and yellows in fall. Sherman Town Park is great for a relaxing day outdoors. You can enjoy walking trails, picnic areas, and a playground for kids.

The Old Store is a historic landmark. This 200-year-old building now serves as a museum and gift shop. It’s a great place to learn about Sherman’s past. Nature lovers will appreciate the Naromi Land Trust trails. These paths offer stunning views of the Litchfield Hills and local wildlife. For a taste of local flavor, visit the Sherman IGA. This family-style market offers fresh produce, baked goods, and American dishes like burgers and fries.

Don’t miss the Happy Rainbows Lavender Farm. You can pick your own lavender and enjoy the fragrant fields in bloom. Remember to check event calendars. Sherman hosts various seasonal festivals and farmers markets throughout the year.

Read our articles on the best things to do in Sherman, Connecticut and best restaurants in Sherman, Connecticut for even more ideas!

Where to Stay in Sherman

Read our article on hotels near Sherman, Connecticut for the best options for your stay. Here’s a short list of some options:

If you’re looking to stay in a vacation home, apartment, BnB, or VRBO in Sherman, Connecticut, we recommend you search on VRBO, Hotels.com, and Booking.com for up-to-date options.

History of Sherman

Sherman, Connecticut has a rich past that will fascinate history buffs. The town was incorporated in 1802 and named after Roger Sherman, a founding father who signed all four of America’s founding documents. You’ll find Sherman’s origins tied to farming and light industry. In the 19th century, the town became known for producing high-quality tobacco leaf.

The area’s landscape changed dramatically in the 1920s. The Connecticut Light and Power Company’s hydroelectric project created Lake Candlewood, flooding the Rocky River Valley.

As you explore, you’ll notice several historical landmarks:

Sherman Congregational Church
Sherman Town Hall
Sherman Green

These sites offer a glimpse into the town’s past and are worth visiting during your trip. Sherman’s cultural scene has deep roots too. The Sherman Players, a local theater group, played a crucial role in preserving the town’s Playhouse. Today, Sherman remains the northernmost and least populous town in Fairfield County. Its small-town charm and preserved history make it a unique destination for your Connecticut adventure.

Towns Near Sherman

Sherman is surrounded by charming towns and cities, each offering unique attractions. Danbury, the largest nearby city, is just a short drive away. You’ll find great shopping at the Danbury Fair Mall and interesting exhibits at the Danbury Railway Museum. New Fairfield, bordering Sherman to the south, boasts beautiful Candlewood Lake. You can enjoy swimming, boating, and fishing in its crystal-clear waters. The town also has excellent hiking trails in Squantz Pond State Park.

Crossing into New York, you’ll discover Brewster. This quaint village is known for its antique shops and cozy cafes. Train enthusiasts will love the restored train station that now serves as a museum.The New York area is within easy reach from Sherman. You’re just a 90-minute drive from bustling Manhattan, where world-class attractions await. Visit iconic landmarks like the Empire State Building or catch a Broadway show.

Other nearby Connecticut towns worth exploring include: