Best Places to Visit in New York State

Searching for the best places to visit in New York State? Well, you are in the right place! Here are my absolute favorite places I discovered while living in New York for 10 years. So where do you go when? In most cases, I highlighted my favorite season in each of these destinations, but most importantly these are all places I keep returning to and I hope you will love them as much as we do.

Best Places to Visit in the Catskills & Upper Hudson Valley

I head here when I'm in the mood for hiking, swimming, antique shops, farm-to-table dining, and cultural landmarks.

1. Narrowsburg

Perched above a dramatic bend in the Upper Delaware River, this tiny hamlet feels like one of the most unspoiled corners of New York I’ve visited, and I think it’s one of the best small-town getaways within a few hours of the city.

About 4 hours from our previous stop in Rochester, Narrowsburg dates back to the early 19th century, and today has a population of just under 500 — small, but full of character!

I loved exploring the Delaware River (I even spotted a few bald eagles!), wandering around Main Street with its cute shops and bakeries, checking out the Delaware Valley Arts Alliance, and enjoying dinner with a view at The Heron, one of the town’s farm-to-table gems.

What I loved best:

I loved visiting in early November when the crowds had thinned and the last of the autumn color clung to the hills.

2. Best Things to Do in The Catskills, NY

Chris and I both absolutely love The Catskills, and have been many times. This region, tucked between forested peaks and charming hamlets, is one of my favorite weekend getaways from n New York City when I want a mix of nature, culture, and cozy comfort.

We drove up from our apartment in Manhattan (just about two hours) and I based myself at the 4-star Hotel Mountain Brook (around $169) where our Superior Main Lodge Room for five days had such a cozy, romantic cabin-like feel with warm woods, and a comfortable sofa in front of the romantic fireplace.

I loved that in the morning, it was just a short drive 7-minute to Kaaterskill Falls (two and a half hours round trip hike), one of New York’s most spectacular waterfalls!

Next day we drove just over an hour to Hanford Mills Museum in East Meredith, a must-visit attraction, one of those hidden gems that feels like stepping straight into a living time capsule. It's actually still a fully operational 19th-century mill!

Afterwards, we drove 1.5 hours south to The Forestburgh Playhouse a must visit stop in The Catskills, where you can choose from Musicals, Plays, Cabaret, Broadway Concerts, and Theatre for Young Audiences! We spent a cozy night at 4-star Inn at Lake Joseph, just 4 minutes from The Forestburgh Playhouse.

What I loved best:

On our second trip to The Catskills (this time during the fall foliage season) we had the most amazing dinner at Peekamoose Restaurant, my personal highlight, a true farm-to-table Catskills experience! We spent two blissful days at the 5-star Urban Cowboy Lodge (around $247/night) just an 8-minute drive from Peekamoose Restaurant.

3. Saugerties, NY

Tucked between the Catskill Mountains and the Hudson River, for me, this is one of the most charming and unexpectedly romantic day-trip destinations in upstate New York.

An easy 20-minute drive north from Woodstock brought us to the heart of historic downtown where we spent the afternoon browsing the shops along Partition Street, enjoying a cozy farm-to-table meal at Miss Lucy’s Kitchen (my son went for the tacos), and then staying for the 48 hour weekend at the beautifully situated 4-star Diamond Mills Hotel (around $316/night), located right above the Esopus Creek Falls.

Next day in the morning, we started at Opus 40, where massive bluestone sculptures rose out of the landscape, creating a surreal, almost otherworldly place to wander together.

My favorite part was walking the winding paths through the stone structures, pausing to take it all in, feeling small in the best possible way as art and nature blended seamlessly around us.

Downtown Saugerties had an easygoing, creative energy, with antique shops, indie boutiques, and cozy cafés that made us slow down and enjoy every stop.

We grabbed lunch at a local spot and shared comfort food by the window, watching the town go by—simple, unhurried, and perfect.

I loved browsing the antique stores and art-filled shops, discovering vintage treasures, handmade pieces, and little finds that felt like they had stories of their own.

A hidden highlight was heading over to Saugerties Lighthouse, walking hand in hand along the narrow trail as the river opened up around us. Learning about the town’s history—from bluestone quarries to river trade—gave the day a deeper sense of place that made everything feel more meaningful.

What I loved best:

Standing by the Hudson as the sun dipped lower, with the lighthouse glowing softly and the water stretching endlessly around us, was my favorite moment—quiet, intimate, and completely unforgettable.

What I loved best:

Walking along the short nature trail out to the historic 1869 Saugerties Lighthouse was my personal highlight! (keep in mind that you have to check the tide schedule before you go).

Best Places to Visit in North Country / Far North

We absolutely love New York’s North Country, a destination defined by vast wilderness and small-town charm.

4. Watertown

When we think about the best places to visit in New York State, this town feels like an amazing underrated gem tucked in the North Country near Lake Ontario and the Thousand Islands.

I loved how Watertown is located just 30 minutes from the Canadian border and only a short drive from the St. Lawrence River, making it a cool and convenient weekend getaway.

We found the downtown area vibrant yet relaxed, with historic architecture, local shops, and interesting restaurants that gave us one of our most joyful small-town travel experiences.

One of my favorite parts was how affordable everything felt, from dining to attractions, which made this destination feel like a brilliant idea for families or couples.

I was surprised by the amount of nature surrounding the city, with spectacular waterfalls, scenic parks, and outdoor adventures that felt hidden yet incredibly accessible.

We spent time exploring nearby Thompson Park, which offered sweeping views of the city and Lake Ontario and felt like an absolute best spot for photos and sunsets.

I think Watertown’s proximity to the Thousand Islands makes it even more exciting, since you can easily add boat tours and island hopping to your dream itinerary.

We also enjoyed how the city balances military history from nearby Fort Drum with a friendly, welcoming atmosphere that felt unique and authentic.

5. Plattsburgh, NY

We love the outdoors, and the farther north you go in New York State, the more spectacular the scenery becomes. One northern gem that often flies under the radar is Plattsburgh, NY. Sitting on the western shore of Lake Champlain and at the gateway to the Adirondack Mountains, Plattsburgh is perfect for travelers craving fresh air, water views, and easy access to nature. Grab your hiking shoes and comfortable clothing—this is an upstate adventure worth taking.

About five hours north of Manhattan, Plattsburgh feels worlds away from the city. We spent two fun days at 3-star Best Western Plus Plattsburgh exploring the Plattsburgh City Beach (one of the largest freshwater beaches in the U.S.), checking out the War of 1812 Museum (free, and strolling through downtown shops.

The lakefront offers beaches, marinas, and peaceful walking paths with views across the water to Vermont’s Green Mountains. In warmer months, kayaking, sailing, and swimming are popular, while fall brings stunning foliage and crisp air. Winter doesn’t slow things down either, with snowshoeing, cross-country skiing, and nearby downhill ski areas.

Nature lovers will find no shortage of places to explore. Just outside the city, Point Au Roche State Park features wooded trails, quiet picnic spots, and excellent lake views, while the dramatic Ausable Chasm—often called the “Grand Canyon of the Adirondacks”—offers hiking, rafting, and jaw-dropping scenery carved by ancient waters. And since Plattsburgh sits right at the edge of the Adirondacks, countless hikes for all ability levels are within an easy drive.

If you’re looking for something less strenuous, downtown Plattsburgh is compact and walkable, with local cafés, breweries, and historic sites tied to the War of 1812. You can enjoy the outdoors without committing to long or difficult hikes, making it a great destination for families and casual explorers alike.

Plattsburgh is easily reached by car via I-87 (the Adirondack Northway), a scenic drive with no tolls north of Albany. Just be sure to plan fuel and food stops ahead of time, as stretches of the drive are remote. Parking around the waterfront and parks is generally affordable or free, depending on the area and season—another win for budget-friendly travelers.

What I loved best:

My personal highlight were the peaceful lakeside trails at Point au Roche State Park (free).

6. Lake George

We recently had the best experience visiting Lake George, a true gem tucked in upstate New York near the Adirondack Mountains.

Lake George was absolutely perfect for our family vacation, with mini golf, arcades, and boat rentals everywhere.

Chris, our son and I drove about four hours north of New York City and honestly the journey already felt exciting and magical.

This place felt like a dream weekend getaway, with vibrant blue water, surrounding peaks, and that fresh mountain air.

I kept thinking how underrated Lake George is, especially since it’s near Albany and still feels hidden.

One of my favorite parts was walking along the village waterfront, which felt joyful, lively, and very family friendly.

We took a boat cruise on the lake and it was an absolute best experience, the views were spectacular and calming.

I loved how affordable everything felt compared to other lake towns, making it a brilliant idea for a romantic trip.

The beaches surprised me most, they were clean, peaceful, and honestly some of the best I’ve seen in New York.

Hiking nearby Prospect Mountain gave us an amazing panoramic view, and it felt like magic at the top.

I found so many cool little shops and unusual diners in town, which made the place feel unique and interesting.

At night we sat by the lake watching the sunset, and it was one of my favorite moments ever.

We spent the first afternoon at Lake George browsing souvenir shops along Canada Street, followed by a hearty lakeside meal at The Lagoon. In the afternoon, Chris and I visited Shepard Park’s waterfront, and then stayed four nights in a beautiful lake view room at the 4-star Lodges at Cresthaven (around $185/night).

What I loved best:

Dinner at Lakeside Restaurant was my personal highlight — the Adirondack trout ($32) was fresh and perfectly prepared, enjoyed with a view of the water as the sun set.

Best Places to Visit in Central & Western NY

Known for rolling farmland, deep glacial lakes, and revitalized downtowns, we love the way this region blends outdoor adventure with history, arts, and a strong food and wine culture.

7. Vestal, NY

We really enjoyed our time here, and it pleasantly surprised me with how much it offers in a low-key, relaxed way.

Set along the Susquehanna River in the Southern Tier, Vestal feels like a town where nature, college-town energy, and everyday local life blend together effortlessly. It’s one of those places that doesn’t try to impress you—but ends up doing exactly that.

I drove about 4 hours northwest from New York City to reach Vestal. If you don’t want to drive, you can take a bus to nearby Binghamton and then a short rideshare into town, which makes the trip fairly straightforward. We spent two stress-free days at Residence Inn by Marriott.

We started the day with a walk along the Vestal Rail Trail, which follows the river and immediately sets a calm, scenic tone. The path is peaceful and well-maintained, and watching the water flow by with tree-lined views felt like an easy way to slow down and settle into the area.

Afterward, we stopped for breakfast at The Shop, a local favorite known for its creative comfort food and welcoming vibe. The portions were generous, the coffee was excellent, and the mix of students and locals gave me a strong sense of Vestal’s community feel. It was the kind of place where you want to linger a little longer than planned.

Spending time near the Susquehanna River—between the Rail Trail and nearby parks—was easily the highlight. The combination of water views, open green space, and gentle hills made it feel restorative without needing a full hike. It’s not dramatic in the way mountains are, but it has a quiet beauty that stays with you, especially if you’re craving a peaceful reset.

What I loved best:

Enjoying a casual bite at The Vestal Bakery was my personal highlight where the selection of treats was irresistible!

8. Things to Do in Rochester

Stretching along the southern shore of Lake Ontario, this city feels like one of the most underrated and unspoiled gems in New York State, and I think it’s one of the best places to experience a mix of nature and culture without crowds.

My first visit was decades ago when I visited the University of Rochester while going to college nearby. Located on the southern shore of Lake Ontario, between Buffalo and Syracuse, Rochester’s often underrated compared to bigger cities, but I think that makes it one of New York State’s best hidden gems.

I learned that this city of roughly 210,000 is known as the birthplace of Eastman Kodak, Xerox, and Bausch & Lomb while we stayed at 3-star Hampton Inn & Suites Rochester for two days.

So what did we see on our 48 hour weekend getaway? Personally, I loved exploring the Strong National Museum of Play with my son, where hours passed in a blink and I was happy my kid learned a lot. If you’re into art, the Memorial Art Gallery is the coolest, with collections spanning centuries. For something outdoorsy, the Rochester's Highland Park and Durand Eastman Park have gardens and lake views (yes, they are lovely even in the winter but be sure to bundle up!).

What I loved best:

In summer, I think the Rochester Lilac Festival is one of the coolest events here!

9. Finger Lakes

Tucked between rolling hills and a shimmering lake, this area is one of my favorites when I want a mix of wineries, farm-to-table food, and outdoor adventure. In addition, I think these lakes are absolutely breathtaking with their deep, blue water, vineyards, and romantic sunsets over the water.

A friend told me about Sonnenberg Gardens & Mansion State Historic Park ($16 Adult admission, open from May 1st to October 31st) and it truly was the ultimate hidden gem in the Finger Lakes region when I visited this August.

To get here, I took a scenic 40-minute drive south from Rochester to Canandaigua, and I spent the afternoon browsing local boutiques on Main Street, walking along the pier on Canandaigua Lake, and then staying two wonderful nights at the 4-star Belhurst Castle (from $195/night), a lovely New York wine county hotel overlooking Seneca Lake.

What I loved best:

Dinner at Stonecat Café was my personal highlight: the pan-seared duck ($34) with local vegetables was unforgettable, paired with a crisp glass of Finger Lakes white.

A downside? Belhurst Castle is such a romantic, magical place, but I found that accommodations and winery tastings were a little pricier than in smaller upstate towns.

10. Cooperstown and Fly Creek Cider Mill

Just an hour and 30 minutes from Albany, I found one of the most perfect day trips from New York - this is a pretty hamlet that captures the essence of rural charm and autumn nostalgia.

A short scenic drive from Cooperstown brought me into the heart of Fly Creek, where the sound of rushing water from Fly Creek itself mingled with the scent of fresh apples and warm cider doughnuts. The undisputed highlight here is the Fly Creek Cider Mill & Orchard, a beloved family-run landmark that has been pressing cider for over 160 years, and I spent a delightful afternoon exploring the cider mill sampling sweet and hard ciders, and browsing the country store packed with local jams, cheeses, and baked goods.

Nearby Cooperstown, NY offers attractions like the National Baseball Hall of Fame and Museum, outdoor activities at Otsego Lake and Glimmerglass State Park, and cultural sites such as the Fenimore Art Museum and Hyde Hall.

What I loved best:

Watching the traditional cider-making process!

Best Places to Visit in the Capital Region / Upper Hudson Valley

Centered around the Hudson River and the state capital, this area is rich in architecture, culture, and easy access to nature.

11. Saratoga Springs

This was my ultimate summer retreat and absolute best place to visit over a long summer weekend with my husband when I moved to New York. Why? For me, the town has great energy, from the opening weeks of the world-famous Saratoga Race Course season to lively outdoor concerts in Saratoga Spa State Park ($10 per car).

Located in upstate New York, not far from Albany and surrounded by rolling countryside, this vibrant town has a magic that feels both historic and exciting at the same time.

We drove 3 hours 30 minutes from our apartment in NYC, checked into the elegant 4-star Adelphi Hotel (around $464/night, Michelin Key award winner), and spent three indulgent days soaking in mineral springs at the historic Roosevelt Baths & Spa ($65 for 40 minutes), strolling along Broadway’s boutique-lined streets, hiking on peaceful trails around Geyser Creek, and eating great hearty American fare at Olde Bryan Inn.

I thought that the Saratoga Farmers’ Market is not to be missed here because one of those places that instantly makes you feel connected to the community, in addition to offering amazing seasonal events and cheap eats!

In addition, my evenings in Saratoga were filled with culture, thanks to performances by the New York City Ballet and the Philadelphia Orchestra at the iconic Saratoga Performing Arts Center.

What I loved best:

For dinner, my highlight was 15 Church, where the scallops ($36) were unforgettable, fresh, delicate, and beautifully plated.

12. Things to Do in Albany

This is one of the most underrated cities I’ve explored in upstate New York, and I genuinely think it’s one of the best low-key getaways in the Capital Region.

After a 2 hours and 30 minute drive from NYC, we stayed at the 3-star Hampton Inn & Suites Albany-Downtown for two nights, which turned out to be a perfect base for exploring the area.

We started by strolling through downtown and around the Empire State Plaza. There, we admired the mix of historic brownstones and bold modern architecture, enjoying how walkable and relaxed everything felt.

My favorite stop was a cozy café along Lark Street, where we shared flaky pastries and warm lattes—it felt like the perfect, unhurried way to start the day together.

We ducked into independent bookstores and vintage shops nearby, laughing as we discovered quirky finds and old records that sparked nostalgic conversations.

A short drive brought us to Washington Park, where tree-lined paths and open lawns gave us a peaceful place to wander side by side and soak in the fresh air.

Later in the afternoon, we ventured just outside the city to a small winery in the surrounding countryside, lingering over a tasting flight and a simple cheese board while dreaming up future trips.

I loved how Albany balanced culture and calm—it felt welcoming and quietly charming, never overcrowded, like a destination still flying under the radar.

We also made time for a local farmers’ market, where fresh bread, seasonal produce, and handmade treats gave us a real sense of the community and a few snacks to enjoy later.

If you are in the mood for hearty NY-style pizza or classic Italian comfort food lunch or dinner (who isn't?!), we love Paesan’s Pizza & Restaurant.

Best Places to Visit in the Lower Hudson Valley / NYC Area

For me, this region delivers the best of both worlds—iconic cultural attractions, diverse food scenes, and neighborhoods full of character, paired with easy access to nature, history, and charming getaways along the Hudson.

13. Things to do in Manhattan, NYC

This place needs no introduction and you simply must add it to your best places to visit in New York State bucket, because after all, it's an exceptional mix of culture, food, art, and energy, where every block feels alive. Chris and I lived in Manhattan for 10 years and on my visit last month we revisited our favorite spots with our teenage son.

I checked into the stylish 4-star Moxy NYC Chelsea, and over five unforgettable days, we wandered the High Line’s urban gardens, browsed Chelsea Market’s gourmet stalls, and recharged with an espresso at Kobrick Coffee in the West Village, a century-old roaster that feels like stepping into old New York. For first-time visitors, I always recommend pairing the High Line + Chelsea Market as a three-hour morning combo, and even if you’re not much of a walker, you can just head straight for the food!

Taking the ferry out to The Honorable William Wall, the floating clubhouse of the Manhattan Yacht Club near Ellis Island, felt like one of the coolest escapes I’ve ever had in the city—half the fun was just getting there. Another favorite water adventure is hopping on a New York Media Boat speedboat tour from Pier 25 in Tribeca, one of the most thrilling ways to see Manhattan’s skyline up close.

Even as a local, I love rediscovering the city’s classics and when I booked a Circle Line Cruise around Manhattan in June, it felt like seeing New York from an entirely new perspective. Of course, no visit to Manhattan is complete without Central Park, my go-to spot for outdoor fun, and after wandering its winding paths, Marea on Central Park South on Central Park South is a must for a refined seafood meal, or for something casual, grab lunch at Whole Foods in The Shops at Columbus Circle on the park’s southwest corner.

Evenings in Manhattan are pure magic, whether catching a Broadway show or soaking in the neon spectacle of Times Square, I always make time for Birdland Jazz Club on West 44th Street, one of the city’s most iconic jazz venues where dinner and live music meet perfectly. For something a bit more romantic, Elsie Rooftop above Midtown makes for an effortlessly fashionable date spot...just remember to reserve your table, especially on weekends (we made this mistake once)!

Afterwards, if you are in the mood for a bit of shopping and want something unique to take home with you, Creel and Gow on East 70th Street is the place to pick up one-of-a-kind treasures and gifts, and when I’m in the mood to “eat my way” through the city, Ahoy New York Food Tours captures everything I love about Manhattan—its flavor, its history, and its infectious energy.

Just north of Manhattan (separated from Manhattan by the Harlem River) Bronx Historical Tours offer a fascinating glimpse into local heritage.

What I loved best:

Celebrating OktoberFest NYC on the waterfront was super fun...okay, maybe it was a bit of a tourist trap (there were plenty of locals too!), but they’re nailing the vibe they are after. Hosted at places like Pier 15 in the Seaport District, OktoberFest NYC brings in the festive spirit of a traditional Bavarian beer garden right in the heart of the city.

14. Things to Do in Brooklyn

Ready for a history-rich city experience? Brooklyn is a real standout. No visit to NYC is complete without a stop my sister-in-law lives, the ultimate creative escape and one of the most unexpectedly soulful places you can explore just across the bridge from Manhattan.

Check prices at 1 Hotel Brooklyn Bridge where I stayed for two days on one of my trips back visiting family, which won the AAA Four Diamond award so you can trust that it's a quality place.

For something totally unique and unexpected just across the bridge in Brooklyn, check out Farm.One in Prospect Heights, Brooklyn. You can book a tour at 625 Bergen Street in Brooklyn, New York where you get to taste what they grow, or check out one of their special events.

When I think of Brooklyn, one of my favorite places to spend a sunny day with kids is Luna Park at Coney Island, just a quick subway ride from Manhattan and the moment I step off with my son near Stillwell Avenue, we feel like we’ve walked into a joyful world filled with colorful rides, boardwalk snacks, and ocean breezes that completely win me over.

On weekends, I love heading to the Brooklyn Flea, which is usually set up near DUMBO and sometimes at Atlantic Terminal because the moment I arrive at Brooklyn Flea, I feel like I’ve stepped into a treasure hunt, with rows of vendors selling everything from vintage clothes to handmade crafts.

Over in Williamsburg, Café Mogador on Wythe Avenue became one of my go-to neighborhood spots, with its inviting décor, Moroccan-inspired menu, and easygoing atmosphere just steps from the waterfront.

And near Brooklyn Heights, stepping into the Brooklyn Historical Society (now part of the Center for Brooklyn History) felt like uncovering a hidden gem because its stately wood-paneled library and exhibits make it a place you’ll want to linger in for hours.

Creative energy thrives everywhere here with FAD Market in Brooklyn makes you feel like you’ve stepped into one of the coolest creative hubs in the city, usually popping up in places like Boerum Hill or Downtown Brooklyn - the market brings together an inspiring mix of fashion, art, and design from local makers.

Tucked in Carroll Gardens, Emma's Torch is another special find, a true hidden gem that doubles as a training ground for refugees building new lives through culinary careers and when we sat down in the warm, welcoming space, I loved knowing that every dish we enjoyed wasn’t only delicious but also part of a bigger mission that supports the community.

Afterwards, BRIC Arts Media in Downtown Brooklyn easily felt like one of the coolest creative spaces in the borough...located right by the Brooklyn Cultural District, it’s a hub where art, music, and storytelling all come together under one roof.

Moored under the Brooklyn Bridge at Fulton Ferry Landing, Bargemusic (a floating chamber music venue) offered not just world-class performances but also unforgettable views of the Manhattan skyline shimmering across the East River.

Pizza Loves Emily in Brooklyn is cozy, lively, and like a perfect slice of New York itself — casual but unforgettable and I stumbled upon some great dining deals here after the holidays, when the city feels a bit calmer but just as full of flavor.

What I loved best:

Last but not least, attending the Brooklyn Film Festival in early summer was one of my most exciting cultural experiences in the borough.

15. White Plains in 48 Hours

As a New York City local, I think this is one of the best gateways to the Hudson Valley. Why? It's super convenient, with a Metro-North stop that makes a trip here cheap and fast.

From Manhattan, it was about a 40-minute drive north to White Plains, a city of around 59,000 that played a pivotal role in the Revolutionary War. Mainly, I wanted my son to see the Battle of White Plains Park (site of the 1776 clash between Washington’s troops and the British), but we found a lot more!

Culturally, White Plains and New York City feel worlds apart, even though they’re barely 25 miles from each other. The pace, the people, the noise level—everything slows down the moment you step off the Metro-North. A New Yorker heading to White Plains might not feel like they’ve left the country, but it definitely feels like leaving the city bubble behind.

Downtown White Plains is compact but lively. You’ve got a walkable core with shops, restaurants, and cafés centered around Mamaroneck Avenue, which comes alive at night with bars, lounges, and casual dining spots.

Driving from Manhattan to White Plains usually takes 45 minutes to an hour, depending on traffic. Rush hour can easily double that time, especially on the Hutchinson River Parkway or I-287. Unlike longer East Coast road trips, tolls are minimal or avoidable, but traffic is still very much a factor—this is suburban New York, after all.

If you don’t want to drive, the train really is the best option. It’s stress-free, frequent, and drops you right in the middle of downtown. That convenience is a big reason White Plains has become so popular with commuters who want more space without fully giving up city access.

What I loved best:

Since food is always on our minds when traveling with our son, my personal highlight was Latin American-inspired lunch at El Primo with excellent fish tacos.

Best Places to Visit on Long Island

Stretching east from New York City, the island offers miles of sandy shoreline, historic communities, and a thriving food scene that we love.

16. Cutchogue on the North Fork of Long Island

Ready for a history-rich, wine-country getaway? I think Cutchogue on the North Fork of Long Island is one of the best hidden gems in New York State, and every time we visit it feels like discovering a secret slice of coastal magic just east of Riverhead and west of Southold.

From our last stop in Greenport, NY, it was less than 20 minutes to reach Cutchogue, a hamlet of around 3,300 people. While we were visiting, I learned that some of the absolute best vineyards and tasting rooms in the state are located right here.

What I love most about Cutchogue is how it delivers an amazing, laid-back experience without the crowds, making it an underrated favorite for a relaxed weekend getaway near the Hamptons but worlds away in vibe.

We found the scenery absolutely spectacular, with rolling vineyards, quiet back roads, charming farms, and Long Island Sound beaches that feel peaceful, romantic, and refreshingly authentic.

One of my favorite things is how close everything feels, since Cutchogue sits right in the heart of the North Fork, making it a brilliant idea for exploring nearby Greenport, Orient Beach State Park, and the North Fork wine trail.

We had a joyful time strolling through local farm stands, where the freshest produce, homemade pies, and seasonal flowers added to the area’s vibrant, small-town charm.

I also found the waterfront here to be one of the coolest surprises, with hidden beaches and calm Sound views that felt unique and perfect for families or a romantic escape.

What makes Cutchogue especially interesting to me is its balance of rural beauty and refined experiences, creating a dream destination that feels both relaxed and elevated.

We loved how the pace slowed instantly, turning even a short visit into an exceptional, soul-soothing experience.

What I loved best:

We loved visiting Suhru & Lieb Vineyards - they have a lovely tasting room, surrounded by 54 acres of vines, including a furnished front patio.

For me, Cutchogue is one of the best places to visit in New York State because it's peaceful, scenic, and hope you will love it too!

For me, the beaches nearby were a highlight as I walked along the calm shores of Peconic Bay and felt like I had the coast to myself, so peaceful, so romantic, and yet perfect for a family picnic too.

17. Fire Island, NY

Fire Island, New York feels like one of the absolute best hidden gems in New York State, and every time I visit I feel that beachy magic kick in instantly. The first time we visited this coastal gem was in springtime two decades ago, with wildflowers on top of some dunes, and very few visitors even though it was a weekend.

Located just south of Long Island and about two hours from New York City, Fire Island is the kind of easy weekend getaway we all dream about.

I love how this barrier island feels worlds away from Manhattan, even though it sits right off the coast of Long Island near Bay Shore.

Fire Island offers one of the most amazing underrated beach experiences, with wide sandy shores, rolling dunes, and that salty ocean breeze I crave.

We found the small car-free communities like Ocean Beach and Cherry Grove to be unique, and full of joyful summer energy.

Walking or biking everywhere felt like a brilliant idea, and it added to the relaxed, romantic, and family-friendly vibe we experienced.

I thought the sunsets here were spectacular, especially near Fire Island National Seashore, which stretches for miles along the Atlantic.

This island is my favorite place to slow down, unplug, and enjoy a cool, affordable escape that still feels special and exciting.

What I loved best:

Dinner at Matthew’s Seafood House was a standout, with just-caught fish and a casual harbor view that felt quintessentially coastal. In addition, ending the day watching pastel sunsets over the Great South Bay was my personal highlight.

18. Greenport, NY

Ready for a history-rich harbor town? Greenport is a real standout. This is a coastal village on the North Fork of Long Island, about 2 hours from my apartment in NYC. We stayed three blissful nights in a Partial Harbor View Balcony King room at the waterfront Harbor Front Inn (around $206/night).

I find strolling along Front Street to be one of my favorite experiences (where we started!) - here local shops, cozy cafés, and historic buildings create a cool and uniquely coastal energy.

Greenport’s proximity to the Long Island Sound makes it spectacular for sunsets, and I swear some of the most amazing golden-hour views I’ve ever seen are right here.

We love that this town is surrounded by vineyards, making it an affordable wine-lover’s dream and one of the best weekend getaway spots in the state.

I always think the nearby beaches are a brilliant idea for families or couples, especially Orient Beach State Park just minutes away.

The food scene feels like a delicious surprise, and I’m constantly impressed by how many interesting, fresh, and seafood-focused restaurants call this small town home.

We find Greenport incredibly romantic, yet still perfect for a family trip, which makes it a rare and exceptional destination.

I personally love how walkable everything is, creating an easygoing experience where slowing down feels natural and refreshing.

What I loved best:

Dinner at Claudio’s was unforgettable — the lobster roll ($38) was overflowing and perfectly seasoned, and eating it just steps from the dock made the experience quintessentially Greenport.

Hi, I'm Ema. I'm the face behind VacationIdea.com. My husband, son are frequent travelers and spent 5 years on the road discovering some of the best places to visit in the USA. We base ourselves in a new place every 4 weeks weeks which has allowed us to experience each destination as a local. I love to chase unique things to do near me and revisit old favorites for a cool, fresh perspective. I'm also eager to learn from my fellow travelers to see what works for people and what doesn't. Whether you like great sunsets, hidden gems, places of mystery, famous attractions, or underrated experiences, here you'll find all of those recommendations from locals that won me over. Let's explore together! More about us.