The 16 Most Charming Small Towns in New York

• Why We Love It: beautiful lake views, historical architecture, seasonal events (Fall Fest, Wtiches’ Walk, Restaurant Week)
• Things to Do: walk on the marina, wine tasting, apple picking
• Where to Stay: Skaneateles Suites Boutique Hotel (from $215/night); Sunset House (from $295/night, sleeps 2); Lake Cottage (from $308/night, sleeps 2)

Skaneateles is one of those towns that feels like it’s straight out of a movie: There’s loveliness at every turn, with lots of historic and perfectly preserved detail. Plus, every shop, restaurant and viewpoint you stumble upon will be better than the next. Speaking of the view, our favorite place to sit and gaze out over the glittering lake of the same name is the waterfront Clift Park, with its adorable gazebo, and neighboring Skaneateles Pier. Once you’ve tired yourself out exploring the dense downtown, enjoy a wood-fired, artisanal pizza at Gilda’s, a favorite amongst visitors and locals alike that offers pick-up and outdoor seating.

• Why We Love It: two-hour drive from Manhattan, mid-century antique shops, contemporary art
• Things to Do: Athens Lighthouse, Olana State Historic Site
• Where to Stay: The Wick (from $259/night); Historic Hudson Apartment (from $198/night, sleeps 4); 1865 Farmhouse (from $128/night, sleeps 2)

This small city (about 6,400 people) is only a two-hour drive from Manhattan and a popular getaway, thanks in part to its mid-century antique shops and lively contemporary art scene. On Warren Street, Hudson’s main drag, is Grazin’, an old-school diner with yummy burgers and cool vibes. Also on Warren is Swoon Kitchenbar, an upscale brasserie with an impressive wine list and delicious cocktails.

• Why We Love It: quaint, on the Hudson with beautiful bay views
• Things to Do: Tivoli Artists Gallery, hiking, kayaking
• Where to Stay: Autocamp Catskills (from $269/night); Luxurious Modern Hideaway (from $971/night, sleeps 6); The Barn (from $495/night, sleeps 6)

What Tivoli lacks in size, it makes up for in quality. The town has seen a renaissance in recent years, with hip new businesses making this approximately 1.5-square mile village popular with New Yorkers who stumble upon it. Case in point: The tiny mobile coffee house concept All That Java, a hipster-meets-traditional Irish pub with serious whisky selection; Traghaven, a very Instagrammable general store; and the oh-so-adorable inside (and out) of seasonal ice cream shop, Fortunes with its service window and yellow spiral staircase. You can also hike and kayak at Tivoli Bays or watch a performance at Kaatsbaan Cultural Park.

• Why We Love It: less than two-hour drive from NYC, scenic river views, historic architecture
• Things to Do: Mohonk Preserve, Samuel Dorsky Museum of Art, Historic Huguenot Street
• Where to Stay: America’s Best Value Inn (from $140/night); Cozy Tiny House (from $95/night, sleeps 2); Modern Tudor Home (from $165/night, sleeps 4)

You can make the 90-minute drive to New Paltz just to stay at the Mohonk Mountain House…we won’t judge. The all-inclusive Victorian-era hotel sits on 40,000 acres on the Shawangunk Ridge and looks like a castle. The sumptuous accommodation offers dozens of fun outdoor activities. New Paltz itself, now a college town, is one of the oldest towns in the U.S. with buildings dating back to the early 1700s. And, its age is a big part of its allure.

• Why We Love It: lakeside setting, many nearby wineries and breweries
• Things to Do: bike tour, Cayuga Lake Wine Trail, Long Point State Park
• Where to Stay: Inns of Aurora Resort and Spa (from $345/night); Cayuga Lake House (from $335/night, sleeps 6); Ravine’s Edge Cabin (from $115/night, sleeps 2)

There are few things more pleasurable than taking a bike tour through this charming village and its main drag filled with historic buildings that line the eastern shore of Cayuga Lake. Mornings in Aurora are well spent sipping a coffee near the peaceful reflection of the lake, while days are best filled with local pottery or painting classes or at wine tastings at one of the many stops on the Cayuga Lake Wine Trail. Enjoy an al fresco meal at a restaurant with innovative cuisine and cocktails like 1833 Kitchen & Bar or getting takeout from Fargo Bar & Grill.

• Why We Love It: historic main street, Hudson River shoreline, great local restaurants
• Things to Do: Saugerties Lighthouse, Esopus Bend Nature Preserve, Seamon Park
• Where to Stay: Comfort Inn (from $329/night); Timberwall Ranger Station (from $257/night, sleeps 6); The Hartwood House (from $298/night, sleeps 5)

Saugerties is a quintessential Hudson Valley town. The village, on the west bank of the river at the mouth of the Esopus Creek, is a historic landmark with a main street full of buildings—antique stores, restaurants, mom-and-pop shops—preserved from the 19^th century. Spend the day at Opus 40, a sprawling outdoor sculpture park or bring a bike to explore one of the many gorgeous bike trails.

• Why We Love It: hidden gem on the Delaware River
• Things to Do: Fort Delaware Museum, stroll the charming main street, walk the scenic route of the Upper Delaware River
• Where to Stay: Moonshadow Inn (from $150/night); The Cabin on Fern Ridge (from $199/night, sleeps 4); Riverfront Cabin (from $208/night, sleeps 4)

If you blink twice, you might miss this Sullivan County hamlet on the banks of the Delaware River. But that would be a shame, because its charming Main Street is packed with cool shops, like Maison Bergogne. The outdoor activities aren’t bad either: You can canoe or kayak down the Delaware or take a relaxing float from Skinner’s Falls with Lander’s River Trips. For lunch, order takeout from The Heron (and be sure to try the fried chicken). For dinner, The Laundrette serves up delicious wood-fired pizzas.

• Why We Love It: preserved historical architecture, breathtaking Hudson Valley views
• Things to Do: hike Breakneck Ridge, West Point Foundry Preserve, Hudson Highlands State Park
• Where to Stay: Cold Spring Hotel (from $203/night); Hilltop Hideaway Forest Villa (from $457/night, sleeps 14); Village Hideaway (from $198/night, sleeps 2)

You’ll feel completely transported in time in Cold Spring thanks to its 200-some preserved 19th-century buildings on the National Register of Historic Places. Visitors also make the trek to hike the surrounding Hudson Highlands. From the top of Breakneck Ridge, a challenging 3.7-mile loop, you’ll have some of the best views of the Hudson Valley.

Explore Hotels in Cold Spring

• Why We Love It: great restaurant scene, antique shops, original home décor stores
• Things to Do: Old Rhinebeck Aerodrome, Ferncliff Forest, Wilderstein Historic Site
• Where to Stay: Mirbeau Inn & Spa (from $620/night); Lemon Cottage (from $253/night, sleeps 4); Rhinecliff on the Hudson (from $424/night, sleeps 8)

Rhinebeck gets a lot of love from travelers, and even boasts presidential ties (former first-daughter Chelsea Clinton tied the knot here). Its popularity is deserved as the home to arguably many of the Hudson Valley’s finest restaurants, home décor, and antique shops and even a charming bookstore to discover your next great read. For $100 per person, you can fly in an old-timey 1929 New Standard D-25 at the Old Rhinebeck Aerodrome, just outside of town, if you’re feeling adventurous and make a reservation ahead of time. Or plan a visit to Ferncliff Forest to climb “the tower” any time of the year; you can also mountain or fat bike here, camp, or just meditate in nature … whatever your outdoorsy heart desires.

• Why We Love It: thriving contemporary and modern art scene, peaceful parks and trails
• Things to Do: Mount Beacon Park, Dia:Beacon galleries, Long Dock Park
• Where to Stay: The Roundhouse (from $439/night); Luxe Loft (from $154/night, sleeps 2); Modern Victorian Guesthouse (from $303/night, sleeps 6)

New York art lovers have been flocking to Beacon—just 60 miles from NYC—since 2003, when Dia:Beacon, a massive museum (the 300,000-square-foot space was once a Nabisco plant) home to contemporary and modern art, opened its doors and put this small Hudson Valley town on the map. At the moment, the museum is open to visitors by advance reservation with a timed ticket, but whether you’re able to snag one during the weekend or not, this beautiful upstate spot still has plenty to offer, including great food and beautiful Mount Beacon Park.

• Why We Love It: close to the city, filled with wineries and farm stands
• Things to Do: sailing, Oysterponds Historical Society, grab snacks at Orient Country Store
• Where to Stay: The Menhaden (from $907/night); Greenport Victorian (from $222/night, sleeps 6); Greenport Loft (from $564/night, sleeps 5)

Forget Napa: New Yorkers looking for a quick wine getaway should look no further than Long Island’s North Fork. The antithesis of its sibling on the south shore, the North Fork is more about wineries, farm stands, sailing and country roads than about the glitz and glam of the Hamptons. Greenport is its seaside center.

• Why We Love It: one hour drive from Manhattan, great for winter activities
• Things to Do: Croton Gorge Park, Van Cortlandt Manor, cross-country skiing
• Where to Stay: The Opus (from $449/night); The Carriage House (from $199/night, sleeps 4); Garden on the Hudson (from $273/night, sleeps 6)

This Hudson River village in Westchester is just a one-hour drive from the city, but will transport you to a completely different world (think: a beautiful arch bridge passing over a dam with gentle flowing water). At the popular Croton Gorge Park, outdoor exploration across 97 acres is a highlight, especially if there’s snow on the ground and you can cross-country ski. Though there’s less of a downtown in Croton-on-Hudson than some of the other spots featured on this list, this charmer still features hip eateries like Croton Tapsmith, a taproom offering cold brews from nearby Hudson Valley producers and locally sourced food options, as well as Ocean House Oyster Bar & Grill. And don’t miss Van Cortlandt Manor, the 18th-century stone house and brick ferry house of New York’s famous Van Cortlandt family.

• Why We Love It: historical architecture and attractions, located on the Canandaigua Lake Wine Trail, plenty of peaceful parks
• Things to Do: Sonnenberg Gardens and Mansion, boat on the lake, Granger Homestead & Carriage Museum
• Where to Stay: The Bella Ella Bed and Breakfast (from $175/night); Bristol Valley Bungalow (from $138/night, sleeps 4); Bristol Street Home (from $225/night, sleeps 6)

Seeing the dreamy Sonnenberg Gardens and Mansion in the flesh would be reason enough to make the drive to this town, which sits on one of the sleepier and decidedly posh-er of the Finger Lakes. The popular attraction is the former summer house of a wealthy New York City family with a Queen Anne-style mansion and nine, distinct formal gardens (our faves being the Japanese and Italian gardens). It is currently open until October 31. Other popular things to do: Taking a pontoon boat out on the lake, which visitors can rent for the day from Sutter’s Marina and drive themselves as long as they are 21+ and have a valid driver’s license. And while most New Yorkers wouldn’t think of driving upstate for authentic Mexican grub, you should not pass go without trying Rio Tomatlan while here.

• Why We Love It: great hiking, vibrant art community, within two hours of Manhattan
• Things to Do: Kaaterskill Falls, Woodstock Byrdcliff Guild, Tinker Street Cinema
• Where to Stay: The Herwood Inn (from $495/night); Little Red House (from $290/night, sleeps 3); Hidden Pines (from $200/night, sleeps 4)

Drive just ten miles west of Saugerties and you’ll find Woodstock. (Both towns are about a two-hour drive from Manhattan and can easily be done in the same weekend.) The town may be best known for lending its name to the iconic music fest—which, fun fact, actually took place 60 miles away in Bethel—but it’s also home to a thriving art scene and has great hiking options nearby, like picturesque Kaaterskill Falls.

• Why We Love It: quintessential Hamptons town, easy drive from the city
• Things to Do: Sag Harbor Whaling & Historical Museum, peruse homewares at Jayson Home, stroll the waterfront marinas
• Where to Stay: Sag Harbor Inn (from $470/night); Whaling Captain Pierson’s Cottage (from $550/night, sleeps 3); Sag Harbor Retreat (from $550/night, sleeps 6)

Whether you love or loathe the Hamptons, one thing most New Yorkers can agree on is that the towns “Out East” including East Hampton, Southampton, and Amagansett are undoubtedly attractive. Still, the clear winner in our hearts is Sag Harbor, both for its adorable Main Street, but also for it’s more laid-back vibes and waterfront marinas, which you’re likely to spot as you take a stroll through the picturesque downtown. The popular Sag Harbor Whaling & Historical museum, housed in a meticulously-preserved mansion, celebrates the town’s whaling past and is open seasonally, but you can also visit it virtually for free anytime. Also on your Sag hit list, especially if shopping’s your thing: Loveshackfancy, a luxury lifestyle store and Jayson Home, a celebrated home décor shop.

• Why We Love It: New York’s first state capital, art enclave, historical architecture
• Things to Do: coffee and antiques at Outdated, stroll through the Stockade district, walk the two main streets
• Where to Stay: Courtyard by Marriott (from $289/night); Kingston Cabin (from $221/night, sleeps 2); Historic Uptown Home (from $272/night, sleeps 5)

Kingston, one of the Hudson Valley’s most popular and evolving towns, overflows with shopping sites sitting on not one, but two separate, picturesque main downtown streets. The artist enclave is a place where you’ll find record and music stores, tattoo parlors, bookstores, and Outdated, a coffee-meets-antique shop housed under the same roof. Architecture buffs will want to take a stroll through uptown Kingston’s Stockade district to see historical old stone houses, specifically at the picture-worthy four corners—the only intersection in the U.S. where these 18^th-century homes sit on all four corners. Characteristic of the neighborhood, visitors will also stumble upon charming streetlights and weathered blue stone sidewalks.