Hotel at a Glance: Deacon Timothy Pratt Bed and Breakfast

Set on a gas-lit street in southern Connecticut, this bed and breakfast was built in 1746 by Timothy Pratt, a carpenter who served as a deacon in the church across the street. Many of the original details of the colonial home have been preserved, including wide-board floors, a beehive oven, and 12 working fireplaces.

• Candlelit breakfast is served on fine china in a fireside dining room (three courses on weekends and home-baked goods during the week).
• Sleep soundly in a romantic guest room with a fireplace, hot tub, and four-poster bed topped with a hand-stitched quilt.
• Old-fashioned ice-cream parlor next door, with a soda fountain installed in 1896

Old Saybrook, Connecticut: Idyllic Seafaring Town with All-American Main Street

Situated at the spot where the Connecticut River meets Long Island Sound, Old Saybrook has nurtured a rich seafaring and fishing tradition for centuries. The town’s most famous resident, however, was a movie star—Katharine Hepburn, who built a sprawling home here with views of the water and the lighthouse. It recently went on sale, listed at $28 million. According to locals, Hepburn swam in the sound nearly every day, well into her 80s, even when the beach was covered in snow.

The oldest town on the Connecticut Shoreline, Old Saybrook has all the trappings of a small New England village: sailboats bobbing in the harbor, clapboard homes, and a quaint Main Street lined with hardware stores, antique shops, and old-fashioned confectioneries. You’re liable to see couples paddling kayaks and canoes around the coves or marching bands serenading families on the town green. Visitors looking for a louder scene can hit the tables at the Foxwoods and Mohegan Sun casinos, both located less than 40 minutes away.

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