Directions from New York, New York to Southold, New York





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


Jericho Pub

Bars – Selden, New York

Jericho Pub - Boasting excellent service and strong drinks, Jericho Pub, located at 600 Middle Country Rd, has a good crowd of regulars and a decent-looking clientele. As an ... More on clubzone

3.5
1 source
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3.5 out of 5
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3.5
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Islands End Golf Course

Golf Courses – Greenport, New York

No noise and not much traffic. More on GolfReview

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  • One of my favorite courses from a playability and summer atmosphere perspective... Not the hardest test by ... More on golflink.com

  • Just playing the par 3 that is along the cliff that overlooks Long Island Sound makes playing this course worthwhile. More on TripAdvisor

Essex Clipper Dinner Train

Trains – Essex, Connecticut

We had a great ride to the "North Pole" with a group. Had a great time, singing and dancing with Sammy Snow... More on TripAdvisor

3.0
10 reviews
1 source
Average Rating
3.0 out of 5
10 reviews
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  • We took the Essex Steam Train (but not the riverboat). It was comfortable, historic, and informative. The v... More on TripAdvisor

  • Take one or both tours in combination for a delightful ... More on TripAdvisor

KOZY Kabin

Bars – Deer Park, New York

Kozy Kabin, located at 1911 Deer Park Ave, is your garden variety pub. It’s not going to win any raves of "Hottest. Bar. Ever.," but it’s a serviceable place to relax and unwind. Just keep your expectations ... More on clubzone

3.5
1 source
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3.5 out of 5
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3.5
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RiverQuest

Things To Do – Old Saybrook, Connecticut

Experience the Connecticut River aboard RiverQuest. 90-minute daytime cruise Essex Harbor and the lower Connecticut ... More on Ctvisit.com

Whistler's Lounge

Bars – Hempstead, New York

3.5
1 source
Average Rating
3.5 out of 5
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3.5
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Parsnip Pub

Bars – Ronkonkoma, New York

Parsnip Pub - While you don’t need to be wearing a suit to get into Parsnip Pub, looking nice will help. The crowd is attractive and the bartenders even more so. If you’re looking for a ... More on clubzone

West River

National And State Parks – Guilford, Connecticut

WEST RIVER, Guilford Intermittent sections from Quonnipaug Lake to Route 1. West River Memorial Park is a linear park (1.2 miles) that offers 200 acres of undeveloped park land, water and brackish marsh for nature-based outdoor recreation. ... More on AnglerWeb.com

Cathedral Pines County Park

Religion and Faith – Middle Island, New York

Very clean too. More on Yahoo! Travel

5.0
1 review
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5.0 out of 5
1 review
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5.0
1+ reviews
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  • Very well maintained and well marked, impossible to get lost. More on trails.mtbr.com

  • We love that the park is very quiet and peaceful. Very clean too. A wonderful place for the family to camp/... More on Yahoo! Travel

Book Swap, The

Book Shopping – Guilford, Connecticut

Used book store that offers a large selection of gently used books in a variety ... More on Yahoo! Travel

Cafe D Isabel Deli

Restaurants – Hempstead, New York

3.5
1 source
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3.5 out of 5
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3.5
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MI Ranchito Bar & Grill

Restaurants – Port Washington, New York

Stay away unless you are fluent in Spanish and like bad food. More on TripAdvisor

3.0
3 reviews
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3.0 out of 5
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  • My son and daughter-in-law discovered this place when they lived in Manor Haven, and it has become our fami... More on TripAdvisor

  • Good for a lunch at work More on TripAdvisor

Mystic River Historical Society

Museums – Mystic, Connecticut

The society, founded in 1973, owns an ever-growing collection of Mystic-related historical books, maps, photographs, and other documents and artifacts contributed by the community. The society maintains a part-time archival and curatorial ... More on Heritage

Branford - Thimble Islands Cruises

Tours – Branford, Connecticut

Daily 45-minute narrated sightseeing cruise of the Thimble Islands aboard the Sea Mist. Foliage cruises, seal watch ... More on Ctvisit.com

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  • There are a number of Thimble Islands Cruises during the summer months which depart from the Stoney Creek Dock. More on PlanetWare