The following list of New York towns to visit is brought to you by New Yorker, Aurie Ceylon from hey, it’s aurie! Read on for some of her top recommendations!

Completely biased opinion: New York State is the best. 

I love exploring New York, and I always say that I will probably (definitely) never live anywhere else, because why would I? From small towns to bustling cities, beaches to mountains, lakes to rivers, and – oh yeah – Niagara Falls! – we truly have it all. 

There are tons of exciting nooks and crannies of New York State to explore, spanning from Long Island to Upstate and beyond… but where can you find the most exciting hidden gems of New York? The obscure, sleepy, and sometimes forgotten small towns!

Rich with history, scenery, architecture, and food, these towns, villages, and hamlets give the Empire State its charm.

Unsure where to begin? Don’t worry, I’ve got your back. Stick with me as we explore a list of unique and fun New York towns you seriously did not know you needed to visit!

1. Beacon

Prepare for some of the most breathtakingly charming views of your entire life (says the wildly unbiased New Yorker who just went to Beacon for the first time ever!).

Without a doubt, Beacon is one of the most idyllic and picturesque towns in New York State. Located on the eastern shore of the Hudson River, Beacon is a small but mighty upstate riverside town that is well worth the trip. Just a 90-minute drive from the hustle and bustle of New York City, Beacon feels like you’ve wandered light years away to a quaint, rustically stunning town that rivals every Hallmark movie you’ve ever seen.

What to do in Beacon: Stroll the winding and seemingly endless Main Street, where you’ll find yourself over-saturated with vintage shops, cafes, record stores, boutiques, and a surprising array of multicultural cuisine. Follow the street through the town (make sure to stop at El Nica in the Hudson Valley Food Hall for the best Nicaraguan steak of your life) until you reach Fishkill River. There, you can marvel at South Beacon Mountain, an overwhelming mass that seems to swallow the town whole. 

Bonus: If you’re there on a Sunday, you must stop by the Beacon Farmers Market!

A perfect day for the rustic wanderer. 

2. Port Jefferson

I can’t gush enough about this adorable maritime town. Located on the north shore of Long Island and originally incorporated in the mid-17th century, this historic waterfront village is nothing short of a tourism hot spot and real estate gem. With stunning ‘painted lady’ Victorians, quaint coffee shops and bookstores, and even the ruins of a cliffside PINK MANSION (rumored to be the former home to a European duchess!), Port Jefferson is full of places to explore. Its stunning location on the Long Island Sound guarantees breathtaking waterfront views, year round. 

What to do in Port Jeff: Spend the day exploring the shops on Main Street (or up and down the residential roads, marveling at historic homes). Grab dinner at PJ Lobster House, one of Port Jefferson’s top-rated places for informal-yet-mouthwatering seafood. (This Long Islander has been dining at the Lobster House since I was a kid, and it never disappoints!) End your night with homemade ice cream and fudge from Port Jefferson Ice Cream Cafe and sunset at the marina. 

Want to stay in Port Jeff overnight? Book a room at Danfords Hotel & Marina, located on the water in the heart of Port Jefferson. Along with an on-site spa, wellness center, and top-rated restaurant, guests can also park their boats in the marina! It doesn’t get more maritime than that.

An idyllic town for the nautical wanderer!

3. New Paltz

Tucked away in the mountainous woods of Ulster County, New Paltz is the quiet college town you’ve been looking for.

With multicolored shops and restaurants lining the main street and Paltz Point views bordering the town, it feels like you’ve basically stepped onto the set of Gilmore Girls.

On top of being a dream for woodsy adventurers, New Paltz is also home to SUNY New Paltz, one of the top liberal arts colleges in the Hudson Valley region. Only a 90-minute drive from New York City, New Paltz has the rustic and historic feeling of a world very far away from the chaos of city life.

What to do in New Paltz: Grab breakfast at Main Street Bistro or B Side Grill, which will undoubtedly be chock full of locals, students, and families (especially on weekends!). Walk along Main Street, exploring the dozens of used bookstores and novelty shops, OR head to Mohonk Preserve and take in over 8,000 acres of forests, fields, and streams. 

Perfect for the woodsy wanderer.

4. Greenport

As a Long Islander who had never been to Greenport, I didn’t know what to think about this mysterious north shore town, especially on a trip during one of the coldest weeks of the year.

But, I’m here to say: Greenport is incredible, even off-season.

Bordered by the Long Island Sound, Greenport Harbor, and Pipes Cove, Greenport is a tiny, picturesque waterfront town that takes a good long snooze in the colder months.

But, while seasonal shops and restaurants close up for the winter, the hamlet thrives on community and local tourism. With only 2,100 residents, winter in Greenport feels like you have the entire incorporated village to yourself! But, not to fear, friends. From wineries to local diners, there is something for every winter wanderer…even those who can’t stand the cold!

Fun Fact: For the history buffs (and perhaps, paranormal buffs?), check out The Old Greenport Jail. Built in 1917, the terribly tiny-and-spooky jailhouse was in use until the Greenport police department was disbanded in 1947, after a history of scandals! Walk by after dark, if you dare!

What to do in Greenport: Start your day with breakfast at the charmingly vintage Crazy Beans (the gluten free pancakes are amazing!), then stop by The Old Greenport Jail for a dose of passerby history. Stroll to the water, then hop on the ferry to Shelter Island, an even quieter and more mystifying seasonal hamlet. Dine on Shelter Island or – for wine lovers – head back to the mainland and check out Kontokosta Winery for breathtaking cliffside views and the best Chardonnay of your life (not kidding). Grab dinner and listen to live music at First & South (get the Mac & cheese!).

After that, grab your bottle of Kontokosta wine and head home! That’s the thing about seasonal towns…they close early!

Ideal for the tiny townie coastal wanderer!

5. Bearsville

Hiking, abandoned hotels, Buddhist monasteries… Am I describing the next big Coen Brothers movie? No, friends. Welcome to Bearsville.

Located in Ulster County, Bearsville is the high altitude meditative escape you didn’t know you had to see. With a population of only 700 and a very wooded atmosphere, it’s easy to miss this tiny hamlet! But, for the wanderers looking for an overlooked adventure, this is the place for you. Take the only slightly terrifying drive up Overlook Mountain, where you will catch glimpses of the breathtaking (and jaw-dropping) views that await you at the very top! 

Fun Fact: For those looking for a bit of ominous history, check out the Overlook Mountain House! Originally built in 1841, Overlook Mountain House was destroyed by not one but TWO fires, one in 1875 and again in 1923! The house was used as a hotel, and even as a meeting place for a top-secret society in the 1920s. It is now part of the Catskill Forest Preserve and sits, undisturbed and publicly accessible, on the Overlook Mountain trail. 

What to do in Bearsville: Hike the extremely steep and rocky trek up Overlook Mountain, stopping along the way to check out the abandoned and ever-spooky Overlook Mountain House! When you reach the summit of Overlook Mountain – for the daredevils – climb the very shaky observation tower for panoramic views of the Catskill Mountains. Once you’ve descended Overlook, stop by the Karma Triyana Dharmachakra Monastery for some much needed (publicly accessible) peace and quiet. 

A perfect destination for the adventurous (and meditative!) wanderer.

6. Kingston

Cobblestone streets, historic colonials, a bookstore winery. Are you sold yet? Welcome to Kingston, New York’s original state capital. From stunning stone-clad architecture to a vibrant downtown center, Kingston is a breath of historically fresh air. 

Fun Fact: Kingston is the only city in Ulster County. It is also the Empire State’s original state capital. But did you know that Kingston was once burned to the ground? During the American Revolutionary War, the city was burned down by the British in 1777 as punishment for aiding Patriots. The city was later rebuilt and flourished in the 19th century for its natural cement, as well as its railroad and canal connections to other hubs around New York State. Today, Kingston is known for its stunning riverfront and mountain views, as well as its incendiary colonial history.

What to do in Kingston: Stroll the stone sidewalks and cobblestone streets, taking in stunning views of 18th century homes, then shop at Kingston’s Uptown Farmers Market and lose your mind buying raw honey and soft cheese (why do soft cheeses always taste better upstate?). When you’ve sufficiently shopped til you’ve dropped, head to dinner at Front Street Tavern or pop across the street to the oh-so-charmingly-historic Hoffman House Tavern, located in a preserved 1679 stone house! Before you call it a night, stop by Rough Draft Bar & Books for – you guessed it – a glass of wine and a quick read.

A great escape for the historical wanderer.

7. Woodstock

Calling all quirky artsy folk! This is the town for you. Located in Ulster County, Woodstock is a bohemian dream.

With a historic town center and the Catskills bordering the town’s edges, it’s easy to imagine meandering through the foliage and marveling at the quaint shops and cafes all day long. A mecca for artists, musicians, and general ‘quirky’ travelers, Woodstock feels like the warm, vibrant, charming, and colorful town you’ve been looking for. 

What to do in Woodstock: Aside from the ever-glorified annual Woodstock Film Festival, take in the charm of boutiques and shops on Tinker Street! Grab the best noodle bowl of your life at Yum Yum Noodle Bar (I’m serious!), and indulge on fudge, truffles, and Woodstock merchandise at one of the many oddball shops.

If you don’t leave with at least one oversized tie-dye shirt and a box of fudge, you did it wrong.

Feeling musical? Take a Rock’N’Roll History Tour, where you’ll stroll the streets and hear stories about Bob Dylan, Janis Joplin, and more!

A must-see for the hippie-dippie wanderer.

8. Montauk

Montauk is the complete opposite of everything glitz and glam. Located on the south shore of Long Island and bordered by the Atlantic Ocean and Block Island Sound, this seaside village is just about as authentic as Long Island gets. For tourists and wanderers looking to avoid the oh-so-trendy neighboring beaches of The Hamptons, you can’t skip this Lobster-encrusted jewel. Yes, lobster.   

Fun Fact: Montauk is the easternmost point in New York State! It has been nicknamed “the end of the world” for its vast and seemingly endless views of the ominous Atlantic Ocean. 

What to do in Montauk: Check out Montauk Point State Park, home to New York State’s first lighthouse, a well preserved relic now protected by the Montauk Historical Society. Commissioned by President George Washington in 1792, Montauk Point Lighthouse is the fourth-oldest active lighthouse in the United States! Located at the easternmost tip of New York, visitors can climb the 137 iron steps to the top, where you can take in 360 degree breathtaking views of Long Island, the Atlantic Ocean, and beyond.

Want to explore “the end of the world” overnight? Book a room at Montauk Manor, Montauk’s national landmark hotel!

This is a must-see for the adventurous (and heights-thrilled!) wanderer.

9. Shelter Island

Remember the tiny waterfront town of Greenport? Well, I’ll let you in on a secret: If you hop on the ferry (all you need is a $3 token!) and cruise 5 minutes across the Shelter Island Sound, you will find yourself on a 12-mile seasonal island, populated by quiet tourists and overflowing with nautical and historic homes.

With a population of over 3,000 Long Islanders, it sounds like Shelter Island should be a bustling town. But, trust me – Shelter Island (especially in the winter months) is as sleepy as sleepy gets. With most of the popular restaurants and breweries shuttered and dark during the off-season, I would definitely recommend saving this trip for the warmer months. 

What to do in Shelter Island: When you’ve finished marveling at the original shutters and wooden shingles of the 18th century homes, stop for lunch at the oh-so-authentic Commander Cody’s Fish Shoppe. This ‘no frills’ local gem is chock full of Long Island favorites. From fried oysters to pulled pork, you’ll leave stuffed and happy. For a cute throwback, pop into Shelter Island Heights Pharmacy, where you can sit at the 1950s-style counter and slurp down strawberry milkshakes and cheese fries. If you’ve still got room for more, stop by Sunset Beach for breathtaking waterfront views and fancy French fare. 

Looking to explore the island overnight? Book a room at Shelter Island House – a top rated B&B-style hotel, located a few steps from Crescent Beach!

This spot is a must for the sleepy upscale townie wanderer.

BONUS: Astoria

Okay, I know what you’re thinking: This is the part where the New York City-based writer talks about how amazing her neighborhood is, right? Absolutely! Let’s talk about Astoria. 

Astoria is located in Queens (one of the five boroughs of New York City) on the East River. A stone’s throw away from Randall’s Island, The Bronx, and Manhattan’s Upper East Side, Astoria is a commuter’s dream come true. It also has breathtaking views, incredible food, and outrageous real estate. Astoria is bordered by 4 other Queens neighborhoods: Long Island City, Woodside, Sunnyside, and Elmhurst. What does this mean? A culturally, religiously, and ethnically diverse metropolis with never-ending things to do, places to go, and food to eat (huzzah!). 

What to do in Astoria: Where do I begin? Bar and brunch hop on Ditmars Boulevard or 30th Avenue, check out the oldest beer garden in New York City at Bohemian Hall & Beer Garden, take in outdoor art installations at Socrates Sculpture Park, dine on incredible Greek food at Gregory’s Corner Taverna or Amylos Taverna (get the lemon potatoes, trust me), then take in the NYC skyline at sunset from the ever-idyllic Astoria Park. 

*Bonus* – There’s even a carnival in the summer!

Astoria is a must for the city-loving wanderer.

Did I miss any of your favorite towns in New York?

Let me know in the comments so I can add more recommendations to the New York list!