Woodstock, Connecticut: A Pink Cottage on Route 169

Thirteen men from Roxbury, Massachusetts settled the plantation in 1686 and first called it New Roxbury; the name changed to Woodstock in 1690 at the suggestion of Judge Samuel Sewall. Massachusetts had bought the land from the Mohegans in 1682, and the town remained part of that colony until 1749, when it incorporated and became part of Connecticut. Farming defined Woodstock through the 18th century; a 19th-century turn to industry made it known for shoe factories before the town reverted largely to farming and became a summer destination for wealthy East Coast families. New York merchant, publisher, and abolitionist Henry C. Bowen built his pink Gothic Revival summer house, Roseland Cottage, in 1846, and opened his adjoining park to the public in 1876. The Woodstock Fair, run by the Woodstock Agricultural Society, reaches its 165th edition in 2026 — one of Connecticut's oldest continuously held agricultural fairs.

Woodstock is a drive-to town: from I-395, take Exit 47 at Putnam, follow Route 44 west about a mile, then Route 171 west about three miles to Route 169 north. Route 169 itself is a 32-mile National Scenic Byway running the length of town and on to the Massachusetts line. There is no passenger rail anywhere in Windham County — neither the CTrail Hartford Line nor Shore Line East reaches this part of the state. From Boston, the drive is about I-90 west to the Auburn interchange, then I-290 and I-395 south; from Providence, I-95 north to I-395 north.

Roseland Cottage, a National Historic Landmark operated by Historic New England, sits on Route 169 with a boxwood garden and what is described as the nation's oldest surviving indoor bowling alley; it hosts an annual Fine Arts and Crafts Festival each October. Henry Bowen's adjoining Roseland Park, opened to the public in 1876 and still run by the Trustees of the Bowen Family Trust, wraps a lake with a nine-hole public golf course — Connecticut's second oldest — plus boating, a playground, and picnic grounds; swimming is not permitted. For lodging, the Inn at Woodstock Hill offers 21 rooms in a country house near the junction of Route 169 and Plaine Hill Road; its restaurant currently serves private events only.