22. Take a two-wheel tour
For casual road bikers, Connecticut contains one of the finest loops in southern New England. A 22-mile ride along the lower Connecticut River takes you past estates that were once owned by ship captains, over a drawbridge to one of the legendary homes of American musical theater, up a hill to a bizarre fieldstone castle, and back across the river on a dollar ferry ride. Start your tour in the historic hub of Essex. In the mid-1800s, this section of the river was lined with more than 50 shipyards. Boats would return from international waters with spices from the West Indies and ivory tusks from Zanzibar. The result of that newly acquired wealth, large Colonial and Federal-style homes that border the water’s edge, can be seen as you make your way north on Route 154. In Tylerville, veer right on Route 82 across a drawbridge into East Haddam, site of the four-story gingerbread Goodspeed Opera House, which opened in 1877 and still delivers three productions a year. Then, make your way up to Gillette Castle. William Gillette amassed a fortune playing Sherlock Holmes at the turn of the last century, but judging from the medieval-style fortress he designed and built between 1914 and 1919, he would have been better suited to playing King Arthur. You can tour the 24-room behemoth overlooking the river and walk the grounds over trestles and through tunnels before biking downhill to the Hadlyme docks. A short ferry ride will bring you to the western shores, where you pedal back to Essex. – Stephen Jermanok
From Essex Square, take North Main Street and continue on River Road; turn right on Essex Street, then right on Route 154, and right again on Route 82 to cross the river. Turn right at the sign for Gillette Castle. After visiting the castle, take a right turn on Route 148 to reach Hadlyme; cross the river via ferry and turn left on Route 154 to backtrack to Essex. Rent bikes at Action Sports in Old Saybrook, 860-388-1291.