17 Charming Small Towns on Long Island to Visit + Hidden Gems

From wine country to historic lighthouses, beaches to art galleries and museums, Long Island is the perfect getaway from New York City. Just a 1-3 hour’s drive (or train ride) from NYC, these towns on Long Island offer interesting cultural sites, fabulous restaurants, and plenty of fun outdoor experiences. For those looking for a break from city living (I know I always do!), consider heading east to one of our favorite charming Long Island towns. 

Table of Contents

Getting Around Long Island Towns

But first, it’s important to note the available methods of getting to and around these different places on Long Island. If you’re like me and don’t own a car because you’re from the city, I know how tricky it can feel to figure out the transportation logistics. But worry not, there are different ways to do it! From trains to buses to car rentals — here is how to visit places on Long Island without owning a car. And if you do have a car, feel free to scroll ahead!

Trains to Small Towns on Long Island

If you’re looking to head east to Long Island, the LIRR can easily take you directly into several towns like Montauk and Greenport. From these train stations, you can either walk around or take an Uber to nearby attractions listed below. Remember that Ubers are way cheaper on Long Island than in NYC. And if you’re going with a friend or two, you can split the cost of an Uber ride from the train station! The LIRR is also relatively cheaper than the other New York train companies. For instance, a ticket from Brooklyn to Greenport (3 hours) is about $15 during the off-peak times.

Please note: most of the hidden gems are 2-3 into the far eastern side of the island but the ride is well worth it!

Buses to Towns on Long Island

If you find the LIRR schedules a little restrictive, consider looking into the Jitney bus schedules. It’s more than the LIRR but can often leave you in places where the LIRR doesn’t go or at a much better time. For instance, the last bus leaving Montauk might be too late or too early for a day trip, but the Jitney will offer you a more reasonable time schedule in which to plan your trip.

Walkability on Long Island

Unfortunately, we live in one of the least walkable countries in the world. But, there are several towns Long Island towns where you can still get around on foot. Charming towns like Greenport, Port Jefferson, and Montauk are perfectly walkable. However, if you’re looking to spend prolonged amounts, it’s important to plan logistics ahead of time for things like grocery shopping and outdoor adventures.

Driving + Road Trips through Long Island

This is, of course, the best way to get around Long Island. With a car, you can venture in and out of Long Island’s small towns to explore the best attractions — all on your own schedule. If you have a car, consider some of our Upstate New York travel guides as well.

More of Our New York State Travel Guides

New York State has some of the most beautiful scenery, treasured history, and amazing experiences. If you’re interested in exploring more of our beautiful state beyond small towns, here are some of our top New York travel guides:

Charming Long Island Towns to Visit

Please note that these Long Island towns are best visited during the warmer months when everything is open and travelers can fully embrace outdoor activities. That means that if you want to visit these places on Long Island before Memorial Day Weekend (last week of May), many businesses may be closed so remember to call ahead!

1. Greenport, Long Island – Cute Walkable Town

Escape into another world by the sea and head to the romantic town of Greenport; ranked as one of America’s prettiest towns. This fishing village is hands down one of the most walkable and best towns on Long Island to visit. It is also super easy to get here by LIRR train from NYC (or other parts of Long Island) since the station is right in the downtown area.


Begin your days in this cute Long Island town by browsing the boutique shops along the main street and admiring the historical homes, built centuries ago. Then stroll the town boardwalk to the sweet antique carousel which is still in operation. Relax here at Mitchell Park and take in the views of the popular public marina.


Do NOT miss out on Greenport’s food! We love to eat a little bit of everything whenever we’re in Greenport. So we created our own foodie tour and stopping at the different restaurants for a little taste of everything at places like:


Visit the East End Seaport Museum and Marine Foundation to learn about the maritime history of Greenport. There is also a huge saltwater aquarium here, a chance to charter a lighthouse cruise, and the annual Maritime Festival in September and includes artisan crafts, live music, unique boat tours, and a wonderful Gala event.


  • Arshamomaque Pond Preserve. The preserve is just a 5-minute drive from Greenport in Southold.
  • Inlet Pond County Park is also another wonderful place to find some fresh air while enjoying scenic woodlands and butterfly gardens.
  • Shelter Island (featured below)

Hotels & Cute Places to Stay in Greenport

  • The Menhaden ★ is located smack dab in the downtown, near the best attractions and restaurants. Perfect if you’re coming without a car. And the design is stunning!
  • Harbor Knoll Bed and Breakfast is a cute cottage-style B&B has a terrace and includes a private beach! A full English/Irish breakfast is included to begin another day of relaxation.

2. Shelter Island, Long Island – A Hidden Gem!

Hop on a $2 ferry from Greenport (listed above) to visit one of the best Long Island beach towns: Shelter Island. This charming island town offers over twenty miles of coastline.


  • Mashomack Preserve: If you love hiking on long island, head to Mashomack Preserve for some hiking along eleven miles of the coastline through scenic trails overlooking coves, bays, harbors, and more.
  • For more adventure, paddle the Coecles Harbor Marine Water Trail. This five-mile water trail takes about 3-4 hours to complete, depending on conditions and abilities. While exploring, you’ll probably see ospreys, fiddler crabs, and maybe even deer and fox.
  • Kayaking Tour ★ : I LOVED kayaking with the folks at Kayak Shelter Island. This is one of our favorite places for kayaking on Long Island. They offer guided tours or you can go on your own. If you’re new at kayaking, I suggest going in the morning on a guided tour because the water gets choppier later in the day. We got a little nervous on the way back with the tides rising. But it was a highlight experience and you get to stop in little islands and beautiful beaches.


  • Choose your beach day by laying out at a popular beach like Crescent Beach
  • Or seek out a quieter, wilder experience at Hay Beach


  • After your outdoor adventures, no doubt you’ll have built up an appetite. Shelter Island has many delicious, unique restaurants to try. The popular and beloved Sunset Beach Restaurant is right on the sand and offers amazing foods inspired by the French Riviera.
  • Shelter Island Craft Brewery use locally sourced ingredients to brew and have a satisfying lineup of changing seasonal beers throughout the year.
  • SALT Waterfront Bar & Grill: This waterfront dining option has also turned bar venue for live music!
  • Commander Cody’s: Outdoor seating for deep fried southern-inspired/seafood.

3. Cutchogue, Long Island – Heart of Long Island’s Wine Country

Cutchogue is a small village (hamlet) located in the heart of Long Island’s wine country. So here, you’ll find several cute tasting rooms, vineyards, and wineries that you can spend your days touring! There are several Long Island Wine Country day trip tours that leave from NYC. I recommend this biking tour that takes you through wineries and farms.

Top Wineries in Cutchogue Area:

Art Spaces in Cutchogue:

You can combine your Long Island wine tasting trail/tour in Cutchogue with a visit to the Alex Ferrone Gallery. This art space is located in a historic building that showcases works of art by contemporary and emerging artists. Here, you’ll see paintings, mixed media, and small sculptural works as well.

For more of the arts in Cutchogue – check out the nonprofit Old Town Art and Crafts Guild where you can admire the work of local artists ranging from jewelry to pottery! They also offer art courses and workshops year-round.

4. Oyster Bay, Long Island ★

Oyster Bay is one of my favorite townships on Long Island, right next to Bayville. The Long Island Rail Road (LIRR) has a stop here and will drop you off in front of Theodore Roosevelt Memorial Park and Beach. The beach is perfect for a day in the sun or for simply watching the boats in the marina.

Oyster Bay also has many walkable options if you base your trip in the thriving downtown. First, Billy Joel has a motorcycle shop here, 20th Century Cycles,  where he stores and works on his own collection of bikes. There’s also a bookstore, yoga studio, popular icecream spot, a cute coffee shop and much more.


  • Sagamore Hill National Historic Site ★ – Tucked into the peninsula. Once the home of Theodore Roosevelt, you can now tour this summer house and explore the natural woods, wetlands, and another harbor and beach nearby. 
  • Planting Fields Arboretum ★ – This gorgeous 409-acre estate is centered around a Tudor Revival mansion. Here, you can take a tour of the grounds, see the historically accurate rooms, and even do yoga on the green.
  • The WaterFront Center: This is a nonprofit that provides kayaking and sailing experiences.

History Attractions in Oyster Bay:

Best Eating & Drinking in Oyster Bay:

  • 2 Spring ★: This spot is a must for food or drinks. Everything was delicious here. Get a reservation or arrive early enough to get seated at the bar.
  • Wild Honey – More traditional spot. Get their traditional plates like blacked cajun fish and beet salad.
  • Cooper’s Bluff: The only waterfront bar in town.  Here’s where all the college kids go to party. But you’ll also see some locals with frozen drinks in their hands and a food truck that serves quick bites. There was a Dave Matthews type band playing. I honestly found it too loud and crowded for my liking, so I left immediately. But a lot of locals love this place!
  • Oyster Bay Brewing Company has some local brews, like the Barn Rocker Ale or a Milkshake IPA.

5. Montauk, Long Island – “The End of the World” ★

At the farthest end of Long Island, sits the romantic town of Montauk. Made popular by the movie Eternal Sunshine of the Spotless Mind, where the two lovers meet on the train ride there. To get a good feel of the town, check out the farming boutiques, cafes/restaurants, and the best beaches in Montauk.

There are so many amazing things to do in Montauk that we dedicated an entire article to it!

Enjoy wonderful outdoor activities in Montauk like the Montauk Point State Park. Visiting the lighthouse here is a classic Montauk must-do. Shadmoor State Park has 2,400 feet of oceanfront beaches and short trails with pretty overlooks of the Atlantic Ocean. Stroll or surf at Ditch Plains Beach, or get up early and enjoy a magnificent sunrise. But my personal favorite in Montauk? This half-day electronic biking tour!

Top Hotels in Montauk

If you want to spend more than a day trip to Montauk, there are a number of interesting places to stay in Montauk, like:

  • Montauk Manor, which sits on 12 acres of beautiful grounds. The resort hotel has its own on-site spa services for guests only, along with a private section of the beach.
  • Gurney’s Montauk Resort and Seawater Spa, which utilizes local natural elements in its wellness treatments, like an ocean-fed seawater pool.

6. Southampton, Long Island

If you’re on your way to Montauk (listed above), consider adding a stop along the way in Southampton. This is the original “Hamptons”.

Enjoy drinks at Duck Walk Vineyards and base the rest of your relaxing day at Cooper’s Beach. If you appreciate cultural heritage, don’t miss the Shinnecock Museum and Cultural Center – a smaller collection of important artifacts from the local Shinnecock tribe. Finally, enjoy browsing in the oldest shopping center in America, Hildreth’s Home Goods, built-in 1842.

Southampton is, without a doubt, one of the best small towns on Long Island to visit.

Top Accommodations in Southhampton

7. Port Jefferson, Long Island ★

Port Jefferson is rated as one of the best towns to live on Long Island since it has an A+ safety rating. This is perfect for a family trip with children, a solo adventure, or just friends day trip. And it’s just a train ride away from NYC by the LIRR.

In Port Jefferson, you enjoy amazing views of the ocean while exploring the downtown area, which was once a shipyard.

Outdoors Activities in Port Jefferson

  • Pirate’s Cove: For a true hidden gem experience, head to Pirate’s Cove (pictured above). This beach area looks like something out of the Mediterranean! You must hike over sand to reach the sand dunes and Pirate’s Cove beach area. There are only 5 parking spots, so get there early or take an Uber to the entrance.
  • Fishing: charter a fishing excursion to really embrace Long Island’s maritime traditions. 
  • Port Jefferson Public Beach: Hang out by the sand to people watch, rent a kayak or just relax in by the sea.

Downtown Port Jefferson Highlights

Events in Port Jefferson

Today, the area offers cultural and recreational events and activities. One such event, Green Fest, takes place in the busy summer months. Another event, Dicken’s Festival, brings tourists to town in the quieter month of December for a special holiday experience. 

Boutique Hotels in Port Jefferson

Stay at The Fox and Owl Inn, an adorable bed and breakfast with a relaxing hot tub and romantic rooms. This inn is run by environmentalists and powered entirely by solar panels. They even compost all organic materials to help grow the native plants that surround the property.

8. Northport, Long Island

Another one of our favorite and best Long Island towns to visit has to be Northport. This town’s main street offers several restaurants, bars, cute shops, and even one of the best breweries on Long Island: Sandy City Brewery! The main street is also within walking distance of the waterfront Northport Village Park (pictured above). You can have a picnic lunch from Organically Yours Cafe to Sunken Meadow State Park for the best views of the Long Island Sound. After lunch, stroll the boardwalk and enjoy the sea-salted air. Or, spend a day at Northport Village Dock.

Northport also has a number of beautiful art galleries. Be sure to visit LaMantia Gallery, Haven Gallery (behind Rockin’ Fish Restaurant), and the Firefly Artists. If you love live music, at the town’s gazebo, concerts usually take place. They are currently paused due to Covid-19 restrictions but will hopefully resume again soon!

Finally, if you love Farmer’s Markets (I do), consider stopping by the Northport Farmer’s Market every Saturday between June and November.

9. Ocean Beach, Fire Island, Long Island

Fire Island is a skinny, thirty-two-mile strip of land just a 20-minute ferry ride away from Long Island’s mainland. Famous for its protected beaches, charming resort communities, and LBGT-friendly scene, Fire Island remains a popular summer destination for New Yorkers. The town of Ocean Beach is the heart and soul of Fire Island and where you can disembark from the ferry.

On the southern tip of Fire Island is Robert Moses State Park. Visitors can spend a day lounging on the beach, swimming, surfing, and boogie-boarding. A short nature walk leads to the Fire Island Lighthouse, a perfect spot for pictures and a great break from the saltwater. 

Head up the island to visit the Sunken Forest, which hosts American holly trees that are over 300 years old.  This specific habitat is found barely anywhere else on the entire earth, so taking a guided trail tour is well worth it.

10. Stony Brook, Long Island – A College Town

One of the nicest college towns on Long Island is Stony Brook, home to SUNY Stony Brook. In addition to being a center for education, this town is also a tourist spot. Here, visitors can enjoy a number of outdoor activities, museums, historical sites, and art galleries such as:

  • Long Island Museum: Exploring a blacksmith shop, 19th century schoolhouse, and more.
  • Stony Brook Grist Mill & Museum: An authentic early American grist mill that still works today. This hidden gem offers a charming look into a day-in-the-life long ago on Long Island. It is open to the public for guided tours with a miller on Sundays (June-October).
  • Reboli Center for Art and History: Admiring gorgeous paintings.
  • Jazz Loft: Learning and enjoying music with this collection of jazz memorabilia as well as a music center.
  • Kayaking: You can go kayaking or paddling at this rental spot. Unless you have quads of steel and the stability of a ballerina, I recommend the kayaking because paddling is exhausting so you’ll miss the nicest parts. #regrets

If you love wine, dedicate some time to visiting Harmony Vineyards. Their tasting room offers waterfront views from a beautiful space that was built around 1690. Enjoying a refreshing glass of rose in front of a 300-year-old fireplace is a uniquely charming experience in this cute Long Island town.

Where to Sleep in Stony Brook

The Stony Brookside Bed & Bike Inn is our favorite place to stay in Stony Brook. Here, you can not only stay but also book custom biking adventures to nearby destinations of your choice.

11. Mattituck – For Wine Country

One of the best towns on Long Island to enjoy the waterfront or a glass of wine, Mattituck is a safe, family-friendly destination. It’s also super close to Greenport and Cutchgue (listed above) so you could pair the three towns together!

After catching up on some much-needed rest, visit the Harbes Family Farm. The farm has operated on Long Island for over thirteen generations. What began as a working farm providing for a family’s needs has evolved into a popular visitor destination. Attend events like watermelon harvest in late summer, and pumpkin harvest in autumn. These events feature live music and locally sourced produce.

In Mattituck for the wine? There are many Mattituck wineries to try. First, try Bridge Lane Wine, and sample all their offerings either in their indoor tasting room or on their patio. Or, bring along a picnic to enjoy on their lawn. 

Laurel Lake Vineyards is another choice, with many New York Wine Classic medals awarded. Enjoy a tour and tasting in a sweet cottage setting. You can also stop into Long Island’s first vineyard, Borghese Vineyard.

Other wineries in the area include:

To experience the outdoors in Mattituck, get the sand in between your toes at Breakwater Beach. Or, hike the shorefront Hallock State Park Preserve. If you’re looking for less excessive exercise, stroll through the Landcraft Garden Foundation, or explore (and take pictures at) the North Fork Sunflower Maze.

Vineyards & Wine Tasting Tours Mattituck

  • Vineyards & Biking tour: A great way of visiting vineyards in Mattituck is on a guided bike tour, where you’ll visit two vineyards where you can taste wine (for an extra cost), and a beach where you can enjoy tasting herb infused olive oils and vinegar. You’ll also visit a farm which sells pies, veggies, jams and fruits. Book this tour here. You could also choose to upgrade to the private option, which includes 2 sets of wine tastings, and photos of your trip as part of the tour. Book the private tour here.
  • Guided tour from NYC: You could also consider this day trip from NYC to some of the best North Fork Vineyards. You’ll get to visit 3 different award-winning wineries near Mattituck, such as Lenz Winery, Raphael Winery, and Osprey’s Dominion. You’ll get to sample 10-12 wines, and enjoy a picnic lunch during the tour. This tour includes transport to and from NYC. Book this tour here.
  • Regular Tour: If you’re looking for a winery tour that starts in Long Island, you could consider this private tour that can cater for 2 to 7 people. The tour includes pick up within the Long Island area, and you’ll get to visit 2 wineries that are within 10 minutes of Mattituck; Osprey’s Dominion Vineyards and Duck Walk Vineyards. Book this tour here.

12. Jamesport, Long Island

Just south of Mattituck, and settled right on the Great Peconic Bay, Jamesport is a hamlet within the larger town of Riverhead. This small town on Long Island has a fine downtown area made up of boutiques and restaurants. Elsewhere, you’ll encounter calm beaches and rolling farmlands, thus making it one of the best towns to live in Long Island.

Also popular with wineries, all of the aforementioned wineries are within driving distance of Jamesport. Jamesport adds their own wineries to the list with Jamesport Vineyards and Little Oak Wood Fired Kitchen. Enjoy delicious drinks along with hand-crafted pizzas made at the center of an 800+ degree wood-fired oven, heated only with local wood. Jason’s Vineyard is another winery to try, with live music, interesting history, and a pet-friendly outdoor patio.

If wine isn’t your favorite beverage, and you’re looking for a special local brew, Try out Jamesport Farm Brewery. Their beers’ ingredients are grown and brewed onsite, making it especially satisfying and fresh. They also host some fun live events like Comedy Night and the East End Market.

There are two truly fantastic places to stay in and near Jamesport. The first is technically located in Aquebogue, just five minutes from Jamesport’s town center. Aqua Beach Hotel sits on a full acre of land right on the Peconic Bay. 

Guests enjoy a private beach, modern rooms and furniture, and gorgeous views of the bay. This boutique hotel has a number of room offerings, including those with water views, garden views, a beach front suite and a rooftop suite. So, be sure to look ahead and choose the layout you would like. 

The second is Jedediah Hawkins Inn. This historic home built in 1863 is now a cozy inn, restaurant, and speakeasy. Enjoy an art gallery in the barn, have a wine enthusiast dinner or clambake, or take a Max Moran painting class on the grounds. 

13. Sayville, Long Island

Another one of our favorite townships on Long Island, Sayville was once an important spot for the timber industry and oysters. However, when the railroad came through, the small town became a popular summer tourist stop. 

For a day touring this Long Island beach town, grab a cup of joe at the Shabby Tabby Cat Cafe, where you can enjoy your coffee and tea with some new feline friends! Then, spend the morning touring Islip Grange, a representation of what this small town looked like in the 19th century. 

After grabbing the town’s best burger at Five Points Cafe for lunch, soak up the rays at the Sayville Bathing Beach. Then, take the ferry over to Fire Island for an evening walk on the beach in one of the state-designated areas.

 Return to the mainland for dinner and drinks at Cafe Joelle, which offers interesting cuisine as well as special cocktails, like Rummin’ Down A Dream- made with coconut-washed rum, lime, rosewater mist, and bright pink dragonfruit. Return here in the morning for a satisfying brunch of omelets, burritos, or Nutella and Strawberry French Toast.

14. Babylon, Long Island

Babylon, NY is made up of a portion of the mainland, as well as portions of three islands. The town was settled in 1689 and got its name from a woman in 1803, who compared the clamorous town to the ancient city of Babylon.

Like Sayville, the arrival of the railroad brought tourists from all over the state and ferried guests across to the islands nearby. Babylon also has a ferry service to Fire Island. 

To experience Babylon, head to  Belmont Lake State Park, and explore 463 acres of creek, lake, wetlands, trails, and more. The park is situated in between highly populated areas and feels like a respite from the hustle and bustle. You may also rent boats and kayaks here to enjoy the water. In the winter, you can cross country ski the summer hiking trails. 

Another interesting thing to do near Babylon is to visit the Adventure Park at Long Island. This outdoor experience takes you zip-lining and climbing, literally through the treetops. It will be an immersive experience, as well as an awesome workout.

15. Sag Harbor, Long Island

One of the nicest towns in Long Island, Sag Harbor is a mix of old tradition and today’s celebrity mansions. Come to Sag Harbor for the food, wine, and art scene, as well as historical sites and hotels.

While checking out Sag Harbor, a wonderful place to stay is Baron’s Cove. This harbor view hotel has fresh, nautical-themed rooms and suites, along with a restaurant of classic Long Island dishes. Ingredients like vegetables, meats, and fish are all sourced from farmers and artisans across the East End. 

You may also want to check out Villa KeyLime, a beachfront vacation home over 3000 square feet. This property is just over a half-mile from Haven’s Beach. In addition, it has its own gardens and private indoor pool, making this the perfect rental year-round. 

To sample some of the best food in Sag Harbor, go to Le Bilboquet, a French Restaurant located right on the harbor. While a little pricey, this restaurant is truly a one-of-a-kind experience. Enjoy mingling while sipping on a few glasses of crisp champagne, or attend a Saturday brunch party.

To experience the best of Sag Harbor’s art scene, take a walk through Grenning Gallery and Tulla Booth Gallery. Both galleries are right on Main Street, so plan on stopping in while you stroll the downtown area.

There are three important historical sites right off of Main Street as well. The Sag Harbor Whaling and Historical Museum,  the home of local artist Annie Cooper Boyd, and the Old Whalers Church are all interesting attractions that will bring you closer to the history of the Hamptons. 

16. Bayville, Long Island

Bayville is one of the best long island towns to get outside and enjoy the scenic views of the North Shore. It’s also one of the most relaxing towns on Long Island. Schedule at least one beach day at one of Bayville’s shores, like Charles E. Random Beach, Bayville Beach, or Centre Island Beach. For a more remote feel, visit Oyster Bay National Wildlife Refuge.

If you’re looking for the perfect place to have a restful stay near Bayville, Book this entire guesthouse in nearby Locust Valley. This sweet cabin has craftsman charm and is only a short walk from another beach. 

Want something a bit more luxurious than rustic? Head a bit further west to the Mansion at Glen Cove. This breathtaking property hosts some amazing weddings, as well as your next vacation. There is a spa, indoor pool, hot tub, and restaurant. You’ll feel like it’s 1922- and that you’re truly a part of that Gold Coast vibe.

17. Sea Cliff, Long Island

The city of Sea Cliff is very close to Glen Cove, and only 25 miles east of Manhattan. One of the nicest towns on Long Island, Sea Cliff is only one square mile large and sits on top of a bluff over 100 feet tall. 

Visit Sea Cliff Beach, or check out Sea Cliff Village Museum. Exhibits include art and historical photography, as well as artifacts from Sea Cliff’s past. Before arriving, call ahead and check their website- the museum is only open seasonally, typically in autumn months. And, there may be Covid-19 regulations in place. 

Follow the shoreline to Fathoms Hotel and Marina in nearby Port Washington. This is a great place to stay while exploring Sea Cliff. This hotel only has six rooms, so you won’t feel enveloped by an enormous abode. This peaceful spot overlooks Manhasset Bay, and, if you arrive by boat, you can dock at the marina.

18. Bay Shore, Long Island

Another wonderful choice of Long Island beach towns, Bay Shore sits just between Babylon to the west and Sayville to the east. Fire Island is across the waters to the south, and you can ferry across to it from town. 

Visit Benjamin’s Memorial Beach and enjoy Bay Shore Marina. The Seatuck Environmental Association is another good stop nearby, on a peninsula just south of Islip. This former family estate turned conservation area now hosts all kinds of endangered animals and protected habitats. You can learn all about their projects at the nature center, and even volunteer in wildlife research, teaching, or hosting events. 

After your day of exploring or volunteering, enjoy a decadent meal at the LakeHouse. Eat a hearty dinner by one of the fireplaces, or a light brunch out on the deck in the fresh salty breeze.

When looking for a place to stay, the Ocean Bay House is a great choice. Situated just under 2000 feet from Benjamin’s Memorial Beach, along Watchogue Creek, this bed and breakfast has nine rooms with lovely views and fresh homemade meals.

19. Garden City, Long Island

Another popular town on Long Island is Garden City. Here, we love to stay at the Garden City Hotel. Opened in 1874, the place has an elegant feel, with much historical charm. The Red Salt Room, located in the resort, is a wonderful place to dine. And, as the hotel is located right at the heart of town, it’s the perfect location to base a wonderful vacation.

While in Garden City, be sure to explore the architecture and stained glass windows of the Cathedral of the Incarnation. And, head to the Cradle of Aviation Museum to learn about Long Island’s unexpected aerospace history. Finally, don’t miss the Hofstra University Museum which houses thousands of artworks on display.

20. Patchogue, Long Island

Patchogue, across the bay from Fire Island, is another of the nicest towns on Long Island. Blue Point Beach and Corey Beach are perfect oceanfront spots to soak up the sun and saltwater. The Swan River Preserve is another great place to get outdoors- while searching for interesting birds, monarch butterflies, and other wildlife.

No matter what time of year you visit, the Garden Farmers Market of Patchogue will be open and operating all weekend. Choose from freshly picked vegetables, stuffed bread, and also pickled items for a locally sourced charcuterie board to build back at your hotel room, or buy fresh coffee beans to take back home. 

21. Cold Spring Harbor, Long Island

The last of our favorite townships on Long Island is Cold Spring Harbor. This is a truly small town with only a population of around 5,000. Thus, there isn’t as much to do as in other parts of Long Island. However, what there is to do is high quality and fun.

First, the Nassau Suffolk Greenbelt trail begins here in Cold Spring Harbor State Park. This trail extends almost twenty miles and cuts across Long Island. For a shorter hike, visit the Wawapek Preserve.

Preservation Long Island is a great stop too, with exhibits and events celebrating all that Long Island once was and could have been. You can also stop by the Cold Spring Harbor Whaling Museum.

Take an eleven-minute ride south of town to Huntington, NY for a truly unique hotel option. Oheka Castle offers luxury stays inside a historic mansion built in 1919. You’ll feel like Gatsby, or Elizabeth Bennett, as you gaze out of your window to the beautiful gardens below.

Other Cute Long Island Towns to Visit:

We have yet to visit the below towns but they are high on my bucket list. Please note that I will continuously update this post as I visit more Long Island towns and cute places. If you like this post, subscribe to our monthly New York travel guides or check out the rest of our New York blog posts.

  • Huntington
  • Port Washington
  • Point Lookout
  • Glen Cove
  • Locust Valley

A trip to Long Island is the perfect way to refresh after busy months stuck in the city. Be sure to add some of the spots on our towns on Long Island map to your small towns in New York bucket list.

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7 thoughts on “17 Charming Small Towns on Long Island to Visit + Hidden Gems

  1. Judy (egan) cuccio says:

    Born and raised in ISLIP N.Y. so were parents,grandparents & the greats. Lots of history in the town. Wish it had been mentioned.

    • Isabelle says:

      We’ll put it on our bucket lists to check out! Haven’t been there since I was little. Thank you for reading and the recommendation. 🙂

    • Isabelle says:

      Yes, there is. Literally Port Jefferson = a port town. In this Long Island town, just 10 second drive from the downtown strip, there is a beautiful beach (pictured above) with kayaks and boats. And 10 minutes driving from the downtown there is a sand dune cove with boats. If some Port Jefferson hotels you’re seeing are $1000 a night, it’s probably because of high peak summer prices + hotels in USA and car rentals have exploded this summer since everyone is staying local due to the pandemic. Danfords is $240/night. Check Airbnb. Open up a Lonely Planet. Do some research. Bon voyage!

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