10 Reasons Why Long Island Should Be on Your Bucket List

So while I write a ton of posts on New York City and spend a lot of my time there I’m actually a proud Long Island native (I actually still live here). It always amazes me how much my friends love it when they visit, always completely surprised at the fact that there’s such a strong culture on the island. Of course, if you’re visiting the Big Apple for the first time you absolutely should spend time in the city, however, a weekend trip to Long Island is something I would highly recommend, and here’s why:

Wine Country

Wine is Long Island’s staple crop, and there are 43 wineries and vineyards all over the island. You can either book a wine tour or, my favorite if it’s warm out, the North Fork Trolley, which for $89 will take you to 3 wineries, a vodka distillery that makes flavored vodkas, a farmers market, and Briermere Farms, where locals flock from all over to purchase the best pie on Long Island. You can also drive down route 25 (Sound Avenue) to come across tons of vineyards and wineries offering live music, dancing, and tastings. Park your car somewhere and walk from vineyard to vineyard.


Even though it’s called Long Island, people seem to have a hard time believing there are beaches here. Whether you want a rocky beach full of colorful pebbles and shells or a soft sandy beach where volleyball and frisbee abound, it’s here. My personal favorites are Smith’s Point and Jone’s Beach (both sandy).

Old-Fashioned Port Side Towns

There are a ton of cute little villages with small but delicious restaurants, homemade ice cream shops near the docks, “malls” selling shells, handmade jewelry, and wooden toys, and outdoor festivals and bands. If you’re looking for the simple life, Port Jefferson is perfect; a quiet town (although an upbeat nightlife scene when the sun goes down), a meditation center, holistic medicine centers, and boutique shopping. In the summer, I really love to go down to Greenport to ride the enormous carousel and then head over to Crabby Jerry’s for some crab cakes, lobster, beers, and music and dancing on the docks.

NYC Nightlife Without the Price Tag

There are so many bars and clubs, both upscale and of the beer and wings variety, that offer open bar specials and extremely discounted drinks. On Thursdays and Saturdays, Blue, a swanky venue in Bluepoint known for its sushi and sexy interior,  hosts a free open bar (on Saturdays it’s ladies only, but you can sneak your man a drink). From Monday-Friday, Four Food Studio and Cocktail Salon, named after its various rooms that represent the four seasons, offers half price drinks from 4-8 and $4 bar menu in Farmingdale.  And on Fridays, Lombardi’s on the Bay, an extremely upscale venue in Patchogue features half off drinks from 4-7pm. Other cheap favorites of mine that are more laid back are the Nutty Irishman in Bayshore, The Harbor Crab in Patchogue, Napper Tandy’s in Miller Place, and Mulcahy’s in Wantaugh.

Nature Abounds

Whether you’re into fishing, hiking, hunting, biking, wildlife, or just relaxing in a beautiful setting, you can do it on Long Island. While most of the hiking trails are flat there are a lot of unique landscapes, which you can read more about by clicking here. My personal favorite hike is Avalon in Stonybrook because Of the diverse landscape in one area, from prairie-like fields to lush forests to wizardly trees and even public art and a meditation labyrinth. Many of these parks and woodlands also have biking trails. For wildlife, you can also visit one of these parks or head over to the Holtsville Ecology Site in Holtsville where they have bears, bald eagles, buffalo, tigers, horses, llamas, and more, all of whom were hurt in the wild and are being nursed and cared for. For a quarter you can even feed the goats.

Art and Culture

Think you need to go to the city for worthwhile museums and art galleries? Because so many celebrities live in the Hamptons, a lot of money has been invested into the arts, and you can visit anything from small art showrooms to expansive art museums. There are also moving museums, such as the Holocaust Memorial and Tolerance Center in Glen Cove, Heckscher Museum of Art in Huntington, Guild Hall in East Hampton, and Garvie’s Point Museum and Preserve in Glen Cove.


During the spring, summer, and fall, you can attend a festival every single weekend. Experience different cultures at the Polish or Greek Festivals, listen to live bands at music festivals, sample wine, pick apples, maneuver corn mazes, purchase art, browse handicrafts, sample craft beer, pig out on lobster…there literally is something for everyone.  Some of the bigger festivals include the International Great Beer Expo, the Jone’s Beach Air Show, the Mattituck Lions Strawberry Festival, and the Long Island Maritime Museum’s Seafood Festival.

Summer Fun

The summer on Long Island is like a different world. Indoor bars, clubs, and restaurants suddenly turn into beachside venues and open air cafes, and flip flops and ripped Abercrombie shorts become evening attire. And of course, the legendary Boardy Barn in Hampton Bays, world-renowned for their $2 beers, happy face sticker attacks, and sloppy afternoons is open for business (this should be on everyone’s bucket list).


While you’ll definitely be able to get your junk food and plastic surgery, there are myriad options for healthy, holistic living. Yoga, Reiki, meditation, and acupuncture centers abound, as well as natural and whole type food shops. Some of my favorite healthy hotspots include Dipamkara Meditation Center in Port Jefferson and Huntington, the Holbrook Wellness Center in Holbrook, and Namaste The Yoga Spa in Plainview.


The island as a whole seems to draw very charitable people, and frequent charity events seem to always be a success. One of the biggest events is the annual Jone’s Beach Making Strides Against Breast Cancer Walk, which draws thousands of participants each year and truly is an inspiring event in a beautiful, coastal setting. There are also many charity Fundraisers, dinners, and bike rides that sometimes involve wine tastings at the end.


  1. I grew up on long island and my parents still live there! (now live in the city) awesome post about the island! people always forget about it when they come into the city!

  2. @Jessica – I’m actually trying to make the move myself for work reasons but it’s hard to look for apartments when I’m always on the road. That being said I would really miss the beaches and wine country on Long Island!

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