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.

• A candlelit breakfast is served on fine china in a fireside dining room (three courses on weekends, home-baked goods during the week)
• Romantic guest rooms feature fireplaces, Jacuzzis, and four-poster beds topped with hand-stitched quilts
• The old-fashioned ice cream parlor next door serves ice cream from a soda fountain installed in 1896
• Most famous former resident: Katherine Hepburn, whose legacy is honored at The Katharine Hepburn Cultural Arts Center in town
Beaches, sightseeing cruises, and waterfront restaurants are all within a mile of the hotel

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

Situated at the mouth of the Connecticut River, Old Saybrook has had a rich seafaring and fishing tradition for centuries. There's a sandbar at the point where the river enters the Long Island Sound, which has prevented the town from ever developing into a major seaport. In turn, residents enjoy relative seclusion here, and the waterway is rarely crowded.

The town’s most famous resident, Katharine Hepburn, built a sprawling home here with views of the water and the lighthouse, which recently went on sale for $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.

Old Saybrook is the oldest town on the Connecticut Shoreline, and it has all the trappings of a stately New England town. Sailboats and the occasional yacht fill the harbor, and there's a classic Main Street, lined with hardware stores, antique shops, and old-fashioned confectionaries. There's an old-fashioned sense of community here, too: elderly couples paddle kayaks around the coves, kids stuff their pockets with fudge and penny candy after school, and marching bands serenade families in the Old Saybrook town green. Those looking for a rowdier scene can hit the tables at Foxwoods and Mohegan Sun Casino, both located less than 40 minutes away.