Crazy Night Out

Fellas–here’s how to have the best night ever on Fire Island

“For just a split second, you forget who you are and you’re just the same as everybody else. And you’re as proud as you ever were.”

Although Fire Island provides some amazing scenery, wildlife, and nature exploring opportunities during the day, it also has a world-renowned night life! From casual bars to high-end restaurants, to one of the most popular gay-friendly meccas on the east coast, Fire Island is perfect for those craving a taste of crazy.

Fire Island is often associated internationally as being America’s gay Disneyland. For more than a century, gay men and women and their hordes of fabulous admirers have flocked to the Fire Island Pines and its equally as-gay neighbor, Cherry Grove, in a seasonal pilgrimage from the mainland that would surely leave Micky and his friends green with envy. The miles of pristine beaches, over-the-top circuit parties, campy cottages, and a plethora of community fundraisers and events are just a smattering of things that keep these two communities on the world map. But more importantly, “The Pines” and “The Grove” have come to define American Gay culture while laying the foundation for the modern gay-rights movement.

Ready for a world of drag queens, drinks, hot hook ups, and acceptance? We’ve put together a guide on how to have the best night of your life on Fire Island! And don’t worry, this guide is gay exclusive. All of the communities listed here are accepting all varying backgrounds and lifestyles, as long as you’re willing to have a good time!

To get straight to the action, we suggest taking the Sayville Ferry right to the Fire Island Pines. Depending on what time you arrive at The Pines, you’ll be able to enjoy some of their fantastic day-drinking spots before dinner. You can find the full Ferry Schedule here.

The Pines

We start our adventure at The Pines, the most gay-centric area of the island. The Harbor walk stretches around the area considered The Pines, however, it is probably more appropriate to call this area The Catwalk. Here, you will see many gay males strutting their stuff up and down the shore line, showing off their physics or looking for a friendly encounter. Close by are stands offering a limited selection of treats and libations that will help keep you hydrated and tipsy while soaking up some sun and enjoying the Speedo-wearing scenery.

The Pines affectionately (or mockingly) has acclaimed that Chelsea on the Bay has certainly come a long way since the Home Guardian Company (HGC) came to be in 1925 and began to develop the community as the next hot resort on the East Coast. It was the 1950s, era of Eisenhower and McCarthy, and homophobia was an ever-present problem that forced gays to suffer silently in the closet.

But a handful of people, such as John Whyte, a former model turned businessman who bought business around the Pines harbor, sought to create an exclusive paradise where gay men and women could come and love themselves–and each other. Soon Whyte, Rock Hudson, Cliff Montgomery, and other Hollywood and Manhattan A-Listers of the day found refuge in the isolation and unique natural beauty of the Pines. The community developed a reputation as one of the few places in the country where gay men could escape over-zealous law enforcement officials and the prying eyes of the general public.

Although The Pines has become famous for their various events, the one most worth mentioning is the yearly July 4th Invasion of the Pines. Started in 1976 when a drag queen was denied entrance into a bar, resulting in “her” friends overwhelming the area in drag, The Invasion of The Pines has become a yearly mega event in which goers celebrate freedom of expression and individuality.

The Blue Whale

If beach lounging is a little too sandy for your tastes, we suggest you do your day drinking at The Blue Whale. The Blue Whale holds a Low Tea each afternoon from 4-8 where you can enjoy the sun and patio, expert cocktails, and an indoor dance floor. Low Tea at The Blue Whale, which happens daily between 4-8 pm, is the perfect location to catch some sun and have some fun before gearing up for your night out. What’s even better? The Blue Whale also offers weekday Yacht Club dining, weekend brunches featuring blues music, and a late-night piano bar on the weekends from 10 pm to 2 am. You can find a list of all their events here.

After spending some time in the sun, you’ll need to fuel up for your night out. After all, what’s a wild night out without a good dinner first? Our recommendation is The Pines Bistro and Martini Bar which is only a few blocks away!

The Pines Bistro and Martini Bar

You certainly don’t want to pass up the Pines Bistro if you are looking for a great way to start your night. Known for its intimate style of dining, the Pines Bistro is the premier Italian restaurant on Fire Island. It may not be the easiest to locate at first, but the reviews speak for themselves. The food and service are fantastic—their call to fame is their martinis. This is the ideal spot to start your night. You can have an excellent dinner while enjoying some of their famous cocktails before heading to your next spot!

After finishing off your dinner and pre-game drinks, your next stop is only a few doors down!

Sip N’ Twirl

All the way through Fire Island’s summer season, Sip·N’·Twirl is the Pines’ most popular nightly lounge and club. Sip·N’·Twirl includes a full-service bar for chatting and socializing, the TWIRLdeck, which is perfect for dancing and casual conversations, and has a giant dance floor with state-of-the-art video and sound system. The music features Fire Island favorites as well as new, up-and-coming DJs, allowing for a variety of tastes and sounds including the latest club sounds from around the world!

After the terrible incident that happened at the Pines, this location was able to be reconstructed within 7 months which ensured that the spirit and vitality of the community stayed alive. Check out all of their events here.

Cherry Grove

If you’re looking for a little more excitement or a change of scenery, we suggest venturing down the trail between The Pines and Cherry Grove.

Often referred to as “The Grove,” Cherry Grove is one of the most famous LGBT communities in the United States. Since 2015, Cherry Grove has been designated as a National Historic Landmark on Fire Island. The Grove is currently a popular summer home location for entertainers and celebrities from all over the world including Wanda Sykes, Victoria James, Hedda Lettuce, Michael Musto, and more.

While Cherry Grove is an exciting destination, the journey there is just as much fun. The stretch of trail between the two meccas is officially called The Judy Garland Memorial Path; however, it is commonly referred to as The Meat Rack. Here, all sorts of casual and interesting encounters accrue, and they are sure to add some tantalizing spice to your night. Take Fire Island Blvd. southbound to reach this path.

The Ice Palace

Previously the site of Duffy’s Hotel which burned down in 1956, The Ice Palace proudly stands in its place. It offers drag shows and other variety acts throughout each day; every visit to the Ice Palace is a new experience. It features a large outdoor deck, swimming pool, pool tables, and a large dance floor. Regulars to The Ice Palace claim that they by far have the hottest bartenders and dancers. Check out all their events here.


Your next location is Cherry’s, visible from the top deck of The Ice Palace. Cherry’s Bar and Cherry Lane Cafe & Restaurant offer reasonably priced cocktails as well as weekly drag shows, theme parties, contests, special guest DJs, and drink specials. They famously serve a Bloody Mary that is spicy enough to get you sweating. What’s even better? There is no cover on Friday’s before 11 pm. Check out more of their events here.

The Morning After

As many wild nights go, it’s hard to know where you’ll end up falling asleep. The Grove has many great summer houses and little houses. Many of these are available to rent and are often done so by those looking to have a good time in the area, so if you do end up going home with someone, you will probably end up in one of these bohemian style summer houses down some wooden walkway, flanked by bamboo trees.

After sobering yourself up, there are plenty of activities and events you can take part in before leaving the island. Boating, fishing, shopping, hiking, and biking are just a few of the daytime activities that Fire Island has to offer. To learn more about them, click here.

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