Settled in 1640, Southold is one of the oldest communities in New York State . The earliest white settlers to arrive here came from New Haven, Connecticut. Standing testimony to the town’s long past is the sleepy Southold Historical Society Museum complex (Main Rd./Rte. 25, 631/765-5500, www.southoldhistoricalsociety.org , 1–4 p.m. Wed., Sat., and Sun., July–Labor Day; suggested donation $2) smack in the middle of the low-key downtown.
Among many historic buildings here are the weathered 1750 Thomas Moore House, the lavishly furnished Victorian Currie-Bell House, and the lovely, hand-hewn Pine Neck Barn. Also on the museum grounds are a working blacksmith shop, a buttery, and a millinery filled with an assortment of 19th- and early 20th-century hats.
A map and more information about the museum complex can be picked up in the 19th-century Prince Building, where the Southold Historical Society is headquartered. Also in the building is the Museum Shop (9:30 a.m.–2:30 p.m. Mon.–Fri.), selling gifts and antiques.
Just north of downtown Southold is the striking Horton Point Lighthouse (off Lighthouse Rd., 631/765-5500 or 631/765-2101, 11:30 a.m.–4 p.m. Sat.–Sun. June–Oct., adults $2), which stands high on a bluff at the end of Lighthouse Road. The first lighthouse on this site was commissioned by George Washington in 1790. The current lighthouse was built in 1857 and is still operational. Painted in stark white and surrounded by rhododendrons, the building overlooks a lonely stretch of beach.
Tours of the lighthouse take visitors through the keeper’s quarters and the working light tower. Downstairs is a small museum filled with artifacts, paintings, and “treasures” from sunken ships.
Run by the Long Island  chapter of the New York State Archaeological Association, the Southold Indian Museum (1080 Main Bayview Rd., 631/765-5577, www.southoldindianmuseum.org , 1:30–4:30 p.m. Sat.–Sun. July–Aug., 1:30–4:30 p.m. Sun. off-season, adults $2, children $0.50) houses an extensive array of Algonquin artifacts. Here you’ll find the country’s largest collection of Native American pottery (from 3000 B.C. to Colonial times).
Housed in a Victorian farmhouse with several fireplaces, four guest rooms (all with private baths), and lots of antiques is the Home Port Bed & Breakfast (2500 Peconic Ln., Peconic, 631/765-1435, www.homeportbandb.com , $200–225 d May–Oct., $150–175 d Nov.–Apr.). The guesthouse is surrounded by woods. Next door is a park equipped with tennis courts and a running track.
North Fork Table and Inn (57225 Main Rd., 631/765-0177, www.northforktableandinn.com , $275–300) offers lovely accommodations. The Table (average entrées $34) at the inn prepares seasonally inspired eats featuring locally grown biodynamic and organic produce, fresh local seafood from the Peconic Bay and Long Island Sound, North Fork  artisanal cheese, and a well thought out wine list. There is also a tasting menu available for lunch and dinner. Check the website for special events, such as beer pairing meals or harvest celebrations.