Long Island's Best Destinations for Summer Fun Without the Sun

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Long Island's Best Destinations for Summer Fun Without the Sun

Long Island is a pretty amazing place. It doesn’t matter where you live or what you’re into, the availability of great food, music, and cocktails is never more than a ten-minute-or-so drive away. We broke down our top-ten area destinations (in no particular order) to make sure you’re taking advantage of all this island has to offer.


(Disclaimer – I live in Patchogue Village and am a Director at the Patchogue Theatre for the Performing Arts)

In case you’ve been asleep for the last ten years, this once-downtrodden village is back with a vengeance. Patchogue has emerged as one of the premier walking villages and nightlife destinations to spend time in on Long Island. It has an amazing live music scene (see 89 North, The Emporium, and the Patchogue Theatre, to name a few), and is one of the best overall food destinations on Long Island. Specifically, try Reese’s 1900 (best burger in town), The Oar (best seafood in town), Pera Bell (upscale pub atmosphere and a good bar crowd), or Hoshi (hibachi and sushi); but feel free to just come down, park, and stop in wherever you heart desires - it’s hard to go wrong. Patchogue’s hugely successful “Alive After Five” street festival has moved to Thursday nights this year and is a can’t miss, and taking the Davis Park Ferry to have dinner and/or drinks overlooking the ocean at The Casino is a personal favorite.

Westhampton Beach

Westhampton Beach is one of my favorite East End destinations. The year-round residents give the village a little bit more of a sense of community than some of the other towns farther east, and there is always plenty to do. In particular, check out the Gazebo Concert Series Thursday nights thru the end of August at 7:30 at the corner of Main Street & Mill Road. The Beach Bakery Café has live music on weekend nights and any of the other dining on Main Street is available , John Scott’s Surf Shack has lobster night every Wednesday, and The Beach Hut at Cupsogue Beach has live music every night starting anywhere from 4 p.m. to 6 p.m. (depending on the night).

Greenport Village

The only true walking village on the North Fork, Greenport has more than enough to keep you busy for a night. Monday nights feature “Dancing in the Park” with live music and dancing at Mitchell Park. Head to Townsend Manor Inn on Tuesdays for live music, drinks, and the Rolling in Dough Pizza truck. On the weekends, a walk down Main St/Rd offers any number of great options for food and drink (too numerous to mention here), but for something new and different, check out The Square. Don’t forget to stop by the Whiskey Wind Tavern (the local dive bar) for late-night pizza and inexpensive drinks.

Shelter Island

With a vibe that’s much more Martha’s Vineyard than Hamptons, Shelter Island is truly a local gem that I don’t think people take advantage of enough. Yes, travel can be a bit of a bear if you don’t keep a boat between the forks, but it’s well worth it and you can always stay the night! Check out the Pridwin Hotel for “Wednesday Night Cookouts,” featuring live music and an all-you-can-eat menu. Salt is another great “by land or sea” option for food, drink, and tunes, or head over to La Maison Blanche for fine French cuisine and an overnight stay!

Port Jefferson

One of Long Island’s quintessential harbor towns, Port Jefferson has something for everyone. Whether you’re looking to party at places like Port Jazz, Billie’s 1890 Saloon, Tommy’s Place, or Lulu’s, a great meal and drinks at places like Pace’s Steakhouse, Pasta Pasta, Ruvo, or The Fifth Season, or to catch a show at Theatre Three, options abound. Additionally, Tuesday nights feature “Movies on the Harbor” and Wednesdays are “Music in the Park,” both at Harborfront Park.

Babylon Village

Another personal favorite that seems to get overlooked by those farther East, this beautiful town boasts a fantastic dining and evening scene, and a number of truly unique settings. Great sushi can be had at Kotobuki, the Babylon Carriage House is a great option for a romantic night out, Barrique Kitchen & Wine Bar has both a good bar crowd and indoor and outdoor dining options, and The Argyle Grill & Tavern boasts an “upscale pub” atmosphere. But these are truly just a few of the fantastic options available so do yourself a favor and head to town without a plan, walk around for a bit and head into the first place that catches your eye (or your stomach)!

Ocean Beach

Drive out to Bay Shore, hop on the ferry and a half hour later you’re here. Ocean Beach is one of the larger Fire Island beach communities and offers a number of options for just about everything. It’s a walking community (feel free to bring a bike) with plenty of bars and restaurants as well as lodging options for overnight stays. For dining, some good options are Matthews Seafood House, Island Mermaid, Maguires Bayfront Restaurant, or Castaway Bar and Grill. After dinner, hit The Sand Bar for live music. If you’re looking to stay don’t expect five star accommodations (this is island living after all), but a couple of good options are the Palms Hotel Fire Island, Houser’s Hotel, or the Fire Island Hotel.


While it’s not necessarily going to work for most for an evening trip, I’d be remiss not to include Montauk on this list. While it’s beginning to get more and more “Hamptonsy,” Montauk has thus far been able to maintain the feel of a local fishing village (but you can certainly plan on paying “Hamptons-like” prices). Some of your best dining options are going to be Dave’s Grill, Backyard, Harvest on Fort Pond, Navy Beach, or Duryea’s Lobster Deck. For drinks, head up to Gosman’s for waterfront, or check out The Surf Lodge, 668 The Gig Shack, The Sloppy Tuna, or Zum Schneider MTK for a great selection of German beer. If you’re planning on staying the night, do yourself a favor and book early. Options are too numerous to mention here so a quick Google search should do the trick.

Sag Harbor

Head out to the Long Wharf and grab some drinks at B. Smith’s while overlooking the water and checking out some of the mega-yachts that call this deep harbor home. Catch a show or comedy night at the Bay Street Theatre, then grab dinner at Madison & Main, The American Hotel, or Tutto Il Giorno (to name just a few!), or try The Beacon if you want to catch an amazing sunset while you dine. If you’re ok with a little smoke (or if you love it), try Cigar Bar for some after-dinner drinks, or head down to Murf’s Backstreet Tavern and finish your night at local go-to Corner Bar.

Hampton Bays

This one is a little out of place on this list because it’s not truly a destination in-and-of-itself, but that doesn’t mean there aren’t great options to be had, spread out though they may be. The most obvious watering hole is probably Tide Runners, but one of my favorites for both dinner and drinks these days has to be Cowfish. While you’re there feel free to take the Rum Barge over to sister restaurant Rumba for a little change of pace and some new faces. Buckley’s Inn Between is a good option for pub fare, and Edgewater Restaurant offers great food, a nice atmosphere, and views of the Shinnecock Bay.

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