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New Milford, Connecticut: Roger Sherman's Town Green

New Milford, Connecticut

Pictures from New Milford

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New Milford Town Green New Milford Green in autumn Housatonic River at Lovers Leap

New Milford was settled in 1707 by John Noble, Sr., of Westfield, Massachusetts, and his eight-year-old daughter Sarah, and the town incorporated in 1712. Its most famous resident, Roger Sherman, lived here before moving to New Haven in 1761 and went on to sign both the Declaration of Independence and the U.S. Constitution; the lot of his former house is the site of today's Town Hall. New Milford is Connecticut's largest town by total area, at 63.7 square miles. Tobacco cultivation and warehouses drove its economy by the late 1800s, alongside factories producing buttons, paint and varnish, hats, and furnishings. During the Revolutionary War the town sent 285 men to fight out of a population of 2,776, and the 7th Connecticut Regiment was raised here on September 16, 1776.

  1. Town history from Indigenous peoples to modern times, plus the colonial Knapp House.

  2. An 1895 iron bridge over the Housatonic gorge and a legendary overlook.

  3. A 365-day-a-year park with walking paths and a former weekend estate.

  4. Community theater since 1967, staging a year-round season.

  5. Downtown's independent movie house on historic Bank Street.

  6. New England's largest weekly flea market, since 1976.

  7. A craft brewery with a full kitchen and live music.

  8. A popular Mediterranean restaurant on Kent Road.

  9. A historic inn on the Village Green, welcoming guests since 1928.

Roger Sherman's town

Roger Sherman is the reason New Milford shows up in national history — before he moved to New Haven in 1761, he lived on the lot that is now the town's Town Hall, and he went on to sign both the Declaration of Independence and the U.S. Constitution. The town's own Revolutionary War contribution was substantial for its size: 285 men out of a population of 2,776, with the 7th Connecticut Regiment raised in town on September 16, 1776. By the late 1800s, tobacco warehouses and factories making buttons, paint and varnish, hats, and furnishings had replaced agriculture as the main economy.

Getting there

New Milford is a drive-to destination: exit I-84 at Danbury and drive roughly 12-14 miles north on US Route 7 or US Route 202 — the two highways intersect and merge to form the town's main corridor — with CT Route 67 also serving the town. New Milford is about 80 miles from Midtown Manhattan. There's no passenger rail station in town; the closest is Metro-North's Danbury Branch terminus in Danbury, about 14 miles south. Tracks running north through New Milford now carry Housatonic Railroad freight only, and a long-studied extension of passenger service to New Milford has never been built.

The green, a flea market, and Main Street

New Milford's long town green anchors the center, with Lovers Leap State Park and its 1895 Berlin Iron Bridge over the Housatonic gorge a short drive away. The Elephant's Trunk Country Flea Market, the largest weekly flea market in New England, marked its 50th anniversary in 2026 with its usual Sunday season, April through December. TheatreWorks New Milford and the Bank Street Theater cover live theater and independent film downtown, and Housatonic River Brewing and Contempo Kitchen & Bar are among the newer names on the dining scene, alongside the historic Homestead Inn.

Frequently asked questions

How do I get to New Milford?
By car: exit I-84 at Danbury and drive roughly 12-14 miles north on US Route 7 or US Route 202. There's no passenger rail station in town; the nearest is Metro-North's Danbury Branch terminus in Danbury, about 14 miles south.
Who was Roger Sherman?
New Milford's most famous resident before he moved to New Haven in 1761. Sherman signed both the Declaration of Independence and the U.S. Constitution; the lot of his former New Milford house is the site of today's Town Hall.
Is New Milford really Connecticut's largest town?
By total area, yes — 63.7 square miles (61.6 of it land, 2.2 water), ahead of second-place Greenwich at 47.62 square miles.
What is the Elephant's Trunk Flea Market?
Billed as the largest weekly flea market in New England, operating since 1976 and marking its 50th anniversary in 2026. It runs every Sunday, April through December, with $4 general admission.
Where can I eat and stay in New Milford?
Housatonic River Brewing and Contempo Kitchen & Bar are two of downtown's newer dining spots. The Homestead Inn, on the north end of the Village Green, has welcomed guests since 1928.

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