Overview
Sherman is a town in the Litchfield Hills in the state of Connecticut. Although Sherman is the smallest town in Fairfield County, it has been nominated as the best small town in Connecticut.
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Plan your trip
Best time to visit & weather
Most comfortable: May–Oct. Summer highs reach about 83°F; winter lows dip to about 15°F. Cold months (Jan, Feb) can bring snow and ice; check road conditions. Wettest: Oct and Aug. (climate data from nearby Waterbury)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- SWF New York Stewart International Airport, Newburgh — 32 mi away. Directions
- HPN Westchester County Airport, White Plains — 37 mi away. Directions
- BDL Bradley International Airport, Hartford — 48 mi away (major hub). Directions
The easiest way to get to Sherman is by car. Coming from the West or East, taking I84 to Danbury, then taking CT-39 through New Fairfield will bring you to the center of the town. From the New York area, taking I-684 North, then taking 22/37 from Brewster will also take you to the town center. From the North, taking Route 7 South, or taking 22 South, then taking 55/37, will both lead to Sherman.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Food for you
American Pie & Company, A family style restaurant with typical American dishes; including Burgers, fries, and a selection of desserts.
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Get in
By car
The easiest way to get to Sherman is by car. Coming from the West or East, taking I84 to Danbury, then taking CT-39 through New Fairfield will bring you to the center of the town. From the New York area, taking I-684 North, then taking 22/37 from Brewster will also take you to the town center. From the North, taking Route 7 South, or taking 22 South, then taking 55/37, will both lead to Sherman.
By plane
- Stewart International Airport in Newburgh, NY, with flights going to Philadelphia, Orlando, Ft. Lauderdale, Atlanta, and Detroit. It is about 70 minutes away
- Tweed New Haven Regional Airport in New Haven, with a flight going to Philadelphia. It is about 90 minutes away
- LaGuardia Airport in Queens, NYC, with dozens of flights going worldwide. It is about 90 minutes away
- Bradley International Airport in Windsor Locks, with dozens of flights going worldwide. It is about 100 minutes away
- JFK Airport in Brooklyn, NYC, with dozens of flights going worldwide. It is about 100 minutes away
- Newark International Airport in Newark, NJ, with dozens of flights going worldwide. It is about 2 hours away
Get around
There is no public transportation in Sherman, so walking or driving is the only option.
See
- As with much of the area, the foliage in fall will be bright reds, oranges, and yellows.
Do
- Sherman Town Park is on the very tip of Candlewood Lake
Eat
American Pie & Company, A family style restaurant with typical American dishes; including Burgers, fries, and a selection of desserts.
Nearby
New Milford
City / town · 5 listings · 5 mi away
Brookfield
City / town · 3 listings · 9 mi away
Kent
City / town · 1 listings · 10 mi away
Danbury
City / town · 26 listings · 12 mi away
Brewster
City / town · 15 listings · 14 mi away
Bethel
City / town · 22 listings · 15 mi away
Southbury
City / town · 15 listings · 16 mi away
Newtown
City / town · 4 listings · 16 mi away
My experience
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