Southold, NY Road Trips
Southold, NY serves as a quiet starting point in the Northeast, connecting drivers to 4 outbound routes across the area. Routes from here tend to cover serious ground — the average trip runs 299 miles, so plan for multi-day adventures. Most routes from Southold, NY head west, giving the route network a clear directional lean.
Photo: Wikimedia Commons
Trip Routes
5
Longest Drive
464.7 mi
Amherst, NY
Quickest Drive
1h 45m
Oyster Bay, NY
Plan Around Southold, NY
Popular Incoming Routes
Useful if Southold, NY is the arrival point and you want the strongest routes into the city first.
Continue From Southold, NY
Good next legs if this city is only one stop in a longer road trip.
Trips from Southold, NY
Driving from Southold, NY
Expect an average of 299 miles and about 6h 25m behind the wheel when leaving Southold, NY. This is long-haul territory. Most routes stretch past the 250-mile mark, so pack snacks and plan fuel stops. The longest mapped route runs 465 miles (9h 55m), while the shortest is just 68 miles.
Popular Destinations
The most popular drives from Southold, NY include Amherst, NY (464.7 mi, 9h 55m), Syracuse, NY (341.4 mi, 7h 11m), Utica, NY (321.8 mi, 6h 45m), and Fair Harbor, NY (67.6 mi, 1h 48m). Most destinations stay within the same state, perfect for exploring the local region thoroughly.
Planning & Costs
Regular gas in NY currently averages around $4.22 per gallon. For the typical 299-mile trip from Southold, NY, budget about $50 in fuel one way, assuming 25 MPG. Longer hauls and premium fuel will cost proportionally more.
Most routes head west — leaving in the morning keeps the sun behind you for a more comfortable drive. These are full-day drives. Start by 7 or 8 AM if you want to arrive at a reasonable hour without rushing.
Frequently Asked Questions
There are 4 mapped routes leaving Southold, NY and 1 routes heading into Southold, NY, covering 5 total connections. Distances range from 68 to 465 miles.
The longest mapped route from Southold, NY covers 465 miles and takes approximately 9h 55m. Shorter options start at just 68 miles.
The average route from Southold, NY runs about 299 miles with a drive time of roughly 6h 25m. This includes both short day trips and longer multi-day drives.
At current gas prices (about $4.22/gallon for regular), the average 299-mile trip from Southold, NY costs roughly $50 in fuel one way, based on 25 MPG. Your actual cost depends on your vehicle's efficiency.
The most popular road trip destinations from Southold, NY include Amherst, NY, Syracuse, NY, Utica, NY and Fair Harbor, NY. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.
Southold, NY by the Numbers
Recent demographic snapshot from the US Census Bureau's American Community Survey.
Population
6,600
Median Income
$114,743
Median Home Value
$762,900
Median Age
51.9
Source: US Census Bureau ACS 5-year (public domain). See our methodology for details.
Southold, NY at a Glance
Founded
1640
Area
156 mi²
Landmarks & Historic Sites
Attractions and heritage-registered places located in Southold, NY.
Horton Point Light
lighthouse in New York, United States
Fort Corchaug Archaeological Site
archaeological site
City data from Wikidata (Q3709805), available under CC0. Photos from Wikimedia Commons under their respective licenses. See our methodology for details.
Traveler Guide to Southold, NY
Southold is a town in Suffolk County, New York. It is the eastern half of Long Island's North Fork.
The town of Southold covers most of the "North Fork" or northeastern peninsula of Long Island. It is more rural in character than most parts of Long Island and is well known for its wineries, farms, and fishing towns. The town's main settlement is the village of Greenport, but it also contains the hamlets of Cutchogue, East Marion, Fishers Island, Laurel, Mattituck, New Suffolk, Orient, Peconic, and Southold.
Although there are a few wineries on the South Fork of Long Island, the Hamptons, the vast majority are located on the North Fork of Long Island. Greenport Skatepark, Ice Skate Rink & Carousel, Greenport, ☏ +1 631 477-1133. Strong's Marine, LLC, Camp Mineola Road, Mattituck, ☏ +1 631 298-4770. This place allows for renting boats and does provide boating lessons. Harbes Family Farm, 715 Sound Ave. (Rte. 48), Mattituck, ☏ +1 631 298-0800. Allows you to pick your own fruit and vegetables as well as flowers. It is open from May till October. The months depend on what you are able to pick. The North Fork of Long Island has many beaches as well as park trails. As well as these beaches and park trails, the North Fork of Long Island is known for their many wineries as well as a small knit community. Sannino Vineyard B&B, 7490 Alvahs Ln (North of RT 48), ☏ +1 631-734-8282. all year. An exclusive Tuscan Suite on a private vineyard Private entrance and balcony overlooking the vineyard King Size bed, 700 sq. feet of luxury Breakfast in Bed $300 avg. Orient Beach State Park, 41425 NY-25, Orient, ☏ +1 631-852-3232. 6AM-8PM. Small waterfront Park known for its pristine views of Long Island Sound and ample fishing. (updated Feb 2024) Horton Point Lighthouse Nautical Museum, 3575 Lighthouse Rd, ☏ +1 631-765-5500. Local history museum housed in an 1857 lighthouse. $5. (updated Feb 2024)
A Touch of Venice, 2255 Wickham Avenue, Mattituck, ☏ +1 631 298-5851. Braun Seafood, 30840 Main Road, Cutchogue, ☏ +1 631 734-7770. Claudio's Clam Bar & Wharf, Main Street Wharf, Greenport, ☏ +1 631 477-1889. Claudio's Crabby Jerry's, Main Street Wharf, Greenport, ☏ +1 631 477-8252. Claudio's Restaurant, Main Street, Greenport, ☏ +1 631 477-0627. Greenport Tea Company, 400 Main Street, Greenport, ☏ +1 631 477-8744. Greenporter Bistro and Wine Bar. Legends, 835 First Street, New Suffolk, ☏ +1 631 734-5123. Lick-itty Splitz, Rte. 25, Mattituck, ☏ +1 631 298-0416. Love Lane Kitchen, Love Lane, Mattituck, ☏ +1 631 298-8989. O'Mally's Restaurant, Rt. 48, Southold, ☏ +1 631-765-2111. The Old Mill Inn, 5775 West Mill Road, Mattituck, ☏ +1 631-298-8080. Orient by the Sea, Main Road, Orient, ☏ +1 631 323-2424. Paganos, Route 25, Southold, ☏ +1 631 765-6109. The Old Mill Inn, 5775 West Mill Road, Mattituck, ☏ +1 631 298-8080. Southold Fish Market, 61859 Main Road, Southold, ☏ +1 631 765-3200. Starbucks, Mattituck Plaza Route 25, Southold.
The entire town is included within the North Fork of Long Island American Viticultural Area and is a popular destination for wine tourism. Ackerly Ponds, 1375 Peconic Lane, Peconic, ☏ +1 631 765-6861. Bedell Cellars, Main Rd., Rte. 25, Cutchogue, ☏ +1 631 734-7537. Castello Di Borghese, Rte. 48 & Alvah's Lane, Cutchogue, ☏ +1 631 734-5111. Comtesse Therese, 1375 Peconic Lane, Peconic, ☏ +1 631 871-9194. Corey Creek Vineyards, Main Rd., Rte. 25, Southold, ☏ +1 631 765-4168. Croteaux Vineyards, 1450 South Harbor Rd., Southold, ☏ +1 631 765-6099. Duck Walk North Vineyard, Rte. 25, Southold, ☏ +1 631 765-3500. Harbes Vineyard, Sound Ave., Rte 48, Mattituck, ☏ +1 631 298-0700. Laurel Lake Vineyards, 3165 Main Road, Rte 25 Laurel, ☏ +1 631 298-1420. The Lenz Winery, Main Road, Rte 25, Peconic, ☏ +1 631 734-6010. Lieb Family Cellar, 35 Cox Neck Road, Mattituck, ☏ +1 631 298-1942. Macari Vineyards and Winery, 150 Bergen Avenue, Mattituck, ☏ +1 631 298-0100. The Old Field Vineyards, 59600 Main Road, Southold, ☏ +1 631 765-0004. Osprey Dominion Winery, Main Road, Rte 25, Peconic, ☏ +1 631 765-6188. Peconic Bay Winery, 31320 Main Rd., Rte 25, Cutchogue, ☏ +1 631 734-7361. Pelligrini Vineyards, 23005 Main Rd., Rte 25, Cutchogue, ☏ +1 631 734-4111 ext 202. Pindar Vineyards, Main Rd, Rte 25, Peconic, ☏ +1 631 734-6200. Pugliese Vineyards, 34876 Main Road, Rte 25, Cutchogue, ☏ +1 631 734-4057. Raphael, 39390 Main Road, Rte 25, Peconic, ☏ +1 631 765-1100.
The Long Island Rail Road offers service on the Main Line - Greenport Branch. 1 Mattituck Station. (updated Feb 2024) 2 Southold Station. (updated Feb 2024) 3 Greenport Station. Eastern terminus of the Long Island Rail Road. (updated Feb 2024) The Cross Sound Ferry offers service from New London, Connecticut to Orient. 4 Orient Point Ferry Terminal, 41270 Main Rd, Orient. (updated Feb 2024)
Travel tips adapted from Southold on Wikivoyage, licensed CC BY-SA 4.0. Content summarized; visit the source for the full article. See our methodology for how we use it.
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