One of the prettiest of the North Fork  hamlets is Cutchogue, filled with white churches, leafy trees, and weathered, shingled homes. The town—named after the Indian word for “principal place”—centers on the village green, in the middle of which are clustered a group of historic wooden buildings (Rte. 25, www.cutchoguenewsuffolkhistory.org , 631/734-7122, 1–4 p.m. Sat.–Mon. July–Aug., call for off-season hours, adults $2, children $1) operated by the Cutchogue–New Suffolk Historical Council.
By far the most interesting of the group is the Old House, which dates back to 1649. Dark and very cozy inside, it’s outfitted with all the luxuries of its day, including wooden paneling, leaded glass windows, and a fluted chimney. The house was “lost” for close to 100 years, but was rediscovered in the 1930s by a WPA worker who noticed its unusual chimney.
Next to the Old House is the 1840 Old Schoolhouse Museum and the Wickham Farmhouse, equipped with furniture and farm implements from the early 1700s. Across the street is the Village Library, housed in a lovely New England–style church. The church was built in 1862 because of a schism within its congregation. The Presbyterian minister was an ardent abolitionist who preached against slavery week after week until the church elders got tired of it and threw him out. The minister then gathered his followers together and built the new church.
Not quite as old as the historic buildings in town, the vintage, chrome-laden Cutchogue Diner (Main Rd./Rte. 25, 631/734-9056, $7) near the village green dates back to the 1920s. The diner’s pancakes and meatloaf are especially good. Also nearby is Braun’s Seafood (Main Rd./Rte. 25, 631/734-6700), where you can purchase clam pies, an East End specialty (these can’t be eaten on the spot; they must be cooked).
Cutchogue—along with Peconic, just down the road—is the center of Long Island ’s wine-producing country. In general, the wineries are open for tastings 11 a.m.–5 p.m. daily, but during the off-season, it’s best to call in advance. Tours can usually be arranged by appointment.
Before you even reach Cutchogue, north along Sound Avenue , you’ll pass the sign Entering Wine Country, and almost immediately you’ll spy Palmer Vineyards (108 Sound Ave., 631/722-9463, www.palmervineyards.com ). One of Long Island’s largest vineyards, it attracts close to 500 visitors on a summer’s day. Palmer offers self-guided tours, a tasting room made up to look like an English pub, and an outdoor deck overlooking its vineyards.
Off Route 25 east of Cutchogue are Peconic Bay Vineyard (31320 Main Rd./Rte. 25, 631/734-7361, www.peconicbaywinery.com ), which produces an especially fine chardonnay; Bedell Cellars (33225 Main Rd./Rte. 25, 631/734-7537, www.bedellcellars.com ), a small but highly regarded winery that has won a number of awards; and Pugliese Vineyards (Main Rd./Rte. 25, 631/734-4057, www.pugliesevineyards.com ), which features a lovely collection of hand-painted bottles containing a chardonnay, blanc de blanc champagne, cabernet sauvignon, and merlot.
Along Route 25 closer to Peconic is the 300-acre Pindar Vineyards (37645 Main Rd./Rte. 25, 631/734-6200, www.pindar.net ), the largest vineyard on the island. Over 20 different wines are produced here annually, and tours run continuously throughout the day. Also popular is the nearby Lenz Winery (Rte. 25, 631/734-6010, www.lenzwine.com ), a 60-acre vineyard with a striking modern main building.
To the north, along Route 48 in Cutchogue, are Castello di Borghese-Hargrave Vineyard (Sound Ave., 631/734-5111, www.castellodiborghese.com ), the oldest vineyard on the island, founded in 1973; and Vineyard 48 (18910 Middle Rd./Rte. 48, 631/734-5200, www.vineyard48winery.com ).