10 Undiscovered Small Towns in New York

When planning a vacation or getaway day trip to New York, or even a day trip from NYC, certain places come to mind first, like the Big Apple itself. Not your traditional visitor hotspots; these ten unique towns, yet to get bitten by the tourist bug, are low in crowds and high in attractions as you venture into the undiscovered reaches of the Empire. The fall is perfect for leaf-peeping through the colors in the Berkshire foothills or hitting the Hudson River walkway.

Amenia

The ambient hamlet of Amenia exudes historic charm and zen-inspiring views. Complement your morning java with pastries from the cozy Peggy's Sweet & Savory and get exploring from the 1920s Beth David Synagogue to the 1850 Indian Rock Schoolhouse and the 1837 Lewis Mumford House, each with a unique backstory to cover. On a summer day, Fudgy's sells irresistible ice cream treats before steak dinner at the Amenia Steak House. Happy to welcome tourists and guide them through its lively attractions and great amenities, venture beyond, and you will discover bale-dotted pastures and lush woodlands of the Berkshire foothills.

Translating from Latin as "pleasant to the eye," it shows. Troutbeck, a hotel on 250 acres, offers a stay amid barns and streams with modern quirks, like a heated pool and Adirondack chairs around fire pits. From old architecture strolls to sifting antique shops, feel yourself part of the painting while fly fishing or horseback riding while hikers hit the 26-mile Harlem Valley Rail Trail, paved right through the village. Not your ordinary outdoor movie theater, Four Brothers Drive-in is a local hotspot for great snacks and new features, with campsites, mini golf, a playground, an arcade, and even an art walk, so there's something for everyone, including a mastodon exhibit.

Chautauqua

Some 16 miles northwest of Jamestown, Chautauqua has that quaint appeal of an underpopulated lakeside town. Tucked to the west in the state along the snaking 18-mile-long Chautauqua Lake, you will discover unique history in a scenic abode of a long-time resort colony, plus easy access to Lake Erie. Established in 1874, the Chautauqua Institution was a lyceum and amusement series popular in the late 19th and early 20th centuries to educate Methodist Sunday school teachers. Having given rise to the Chautauqua movement that replicated throughout the US, the institution remains the center of culture, with a resort area and a summer program of art, drama, and music.

While some enjoy the resort's youth activities, many are happy to discover its long-favored businesses. Chautauqua Bookshop and St. Elmo Spa are perfect for enjoying a winter afternoon with a group of friends or a couple. In the summer, enjoy swimming from Pier Beach, fishing on the lake, and nearby trails, with Camp Prendergast just down the road. Within, the village of Mayville features Snug Harbor Marina, just north of the Miller Bell Tower, a scenic landmark against the blue of the lake. The iconic Chautauqua Gorge State Forest sprawls southwest in a beautiful, peaceful nature preserve with a creek, wildlife trails, and free camping. You'll be happy to return for the informal yet gourmet scene at Andriaccio's Restaurant, which includes Italian-style pizza, seafood, and steak.

Homer

Homer, a Central New York town some 30 minutes from Syracuse, was settled in 1791 along the Tioughnioga River. The locals enjoy easy river access just a block from the Main between shopping and dining in the largely 19th-century downtown. Centered around the Village Green, its churches and old houses will fill up your Instagram feed with beauties like the giant Gothic-style former church from 1893. Attracting culture fans to this neck of New York’s woods, the Center for the Arts of Homer is a bustling venue with a variety of works and regular shows, including performers from the past like Judy Collins and David Sedaris.

Homer offers a quaint feel as one of the largest among the surrounding villages, with many locals who commute for work south to Cortland and Ithaca or north to Syracuse. With vibrant city-like attractions throughout its few hamlets, Little York embraces Little York Lake to the north with a few arts and crafts shops plus a garden store. Many enjoy the year-round farm market and bakery for only what is freshly baked and local from the large greenhouse, the surrounding rolling hills, and valleys, primarily agricultural. In the winter, a string of skiing city folk flock to the neighboring Greek Peak Mountain Resort, Song Mountain Resort, and Labrador Mountain.

Narrowsburg

This town across Pennsylvania on the Delaware River, between the Catskill Mountains and the Pocono Mountains, is the "pioneer hotspot.” Just 2.5 hours from the Big Apple, the winding drive through the mountains, reflecting its name, induces anticipation for the adventures ahead. Greeting you with lots of peace signs and doves painted on the barns, you've hit a not-so-ordinary town, even next to the original site of the 1969 Woodstock Festival in Bethel Woods. This sprawling river stretch is a summertime tourist magnet, drawing urban escapees for waterside recreation. Enjoy kayaking and rafting with a picnic after a stroll to the Upper Delaware River for scenic views.

With an influx of new shops, restaurants, and entertainment along its mighty Main, Narrowsburg is among the coolest getaways from NYC. From a variety of museums to a culinary scene, plus the Tusten Theatre on Bridge Street, Fort Delaware Museum features a 1700s fort. Don't miss The Heron, one of the region's best restaurants, while the options to wind down include the Maisonette or the historic School House Cottage. Art connoisseurs enjoy sifting through various styles at Delaware Valley Arts Alliance and local works at the River Gallery. Journeying home, Hawk’s Nest is one of the state's best drives via Route 97 through Barryville, along the Delaware River, into Port Jervis.

Northport

Venturing into the undiscovered portion of Long Island, steering clear of the Hamptons, the waterfront village of Northport is Huntington’s most populous, with some 7,250 residents. Looking for a sea-salty breeze on a stroll with unobscured views, low crowds, and vibrant attractions? If you love the ocean, you will not be remiss in the laid-back feel of this seaside community with rich maritime history and great cuisine. Sprawling the eastern side of Northport Harbor, the ambient town was formally incorporated in 1894 as a bustling shipbuilding hub. Start at Copenhagen Bakery on Woodbine Avenue and hit Main Street for unique shops and art galleries.

After a relaxing afternoon by the stunning harbor at Northport Park, the Purple Elephant offers a beachy vibe with its mascot on the porch and a patio to enjoy thoughtfully sourced, Latin-inspired dishes, including vegan options. Robke's, a long-favored for hearty Italian meals in a warm parlor setting, will undoubtedly make you thirsty for either Del Vino Vineyards or craft brews at Sand City Brewing Co. From the Asharoken Beach Park to Crab Meadow Beach for swimming next to a boardwalk, a playground, trails, and a kayak launch, play a round at the neighboring Crab Meadow Golf Course or explore the breathtaking Jerome A. Ambro Memorial Wetland Preserve.

Rosendale

Home to the grandiose Vanderbilt Mansion in the countryside and one-of-a-kind outdoor attractions, Rosendale has something iconic for every culture and nature lover. The Hudson River walkway offers breathtaking views on an easy stroll or pedal, while the Mohonk Preserve is a sprawling nature reserve with 75 miles of carriage trails and cliffs. Others know this small town for its bridge and theater, the Rosendale Trestle. A one-time 150-foot-high, 940-foot-long railroad bridge is open for hikes and bike rides with extraordinary views of Rosendale Village and Rondout Creek. Established 75 years ago, the three-story family-run Rosendale Theatre offers a cozy feel, new releases, and second-run films, plus an array of plays and events.

Formerly in cement manufacturing, now the home of artists and entrepreneurs, enjoy the vibrant compilation of homes and businesses along the Main, with stops to shop like Postmark Books for a novel and bouquet at the in-house florist. Nearby, Women’s Studio Workshop flaunts rotating gallery exhibits, while the cute Alternative Baker is famous for its lemon cakes. Having been closed for over half a century, the historic Widow Jane Mine offers highly demanded tours around its industrious past, doubling as a unique venue for events like the annual Subterranean Poetry Festival. After all the discoveries, Willow Kiln Park is a great place for a breather, with benches, picnic spots, and a bandstand.

Pawling

Just 90 minutes on Metro North from Grand Central, Pawling is perfect for leaf-peeping through the colors of fall in the foothills of the Berkshires. Hikers along the Appalachian Trail have their paws on Pawling, which passes the iconic Dover Oak nearby. Featuring a plethora of outdoor activities like horseback riding and a fantastic culinary scene, brunch at McKinney & Doyle is a must. Just order the strawberry cream cheese pancakes, and you'll be full until a great Friday night of live music and great brews at Daryl’s House. Hobbit House hosts an unforgettable overnight party for six people, starting at $500 per night, while Pawling Retreat is truly a steal at $400 per night for a dozen friends.

The undiscovered feel of Pawling is apparent in low tourist crowds. High in tourist attractions, Pawling attracts hikers, entertainment seekers, and families through its two-square-mile village, the commercial hub. Once a haven for reticent celebrities, the large properties exude quaintness reminiscent of the past, blending into a new wave of cafés and shops for every modern traveler, like O'Connor's Public House and the Sunflour Bakery. Framed in nature by pretty preserves like Pawling Nature Reserve and West Mountain State Forest, enjoy summertime trails with local wildlife and swimming at Pawling Recreation and Lakeside Park in the summer.

Stone Ridge

This undiscovered town is a treasure trove of romantic architecture and a celebrated local food scene. Right across the highway from High Falls, it's easy to combine the two towns next to the unspoiled views along Rondout Creek. Hasbrouck House, one of the many Dutch stone houses, embraces the elegance of the bygone era, while Duchess Farm Equestrian Center offers a fun pursuit for families or couples. Grab lunch at Hush or from the popular Cherries Roadside and General to enjoy after a hike along Rest Plaus O&W Rail Trail to an open area with pretty views. Butterfield, a fine dining restaurant in a beautiful Dutch stone house, offers an unforgettable and supremely tasty dinner, inspiring a romantic date or a close gathering with your loved ones.

This historic hamlet in the town of Marbletown has enough to discover over a weekend getaway from the city along its centuries-old homes, winding roads, and bucolic landscapes. Stop by the friendly Grassroots Farm or pick your own locally grown foods at the family favorite Stone Ridge Orchard, which also serves a home-cooked meal in the outdoors. For a longer trip, cross the river for a fun evening at the hip Spy Social Eatery and Bar. The Sheeley House can be your homey stay to unwind right by the creek and explore the sprawling Callisto Hudson Valley to the east. Minutes north, Marbletown Town Park in Kingston is a large, dog-friendly area popular for outdoor recreation among locals from all three communities.

Tivoli

Part of the larger Red Hook, Tivoli feels like a sleepy village of just over 1,000. Spanning a super walkable, less-than-two-square-mile area, its hip new businesses and creative outlets can scratch every traveler's itch on a weekend trip upstate. Squint and you can see Saugerties Lighthouse along the banks of this undiscovered town along the Hudson River. From Tivoli Park at the heart, it is just a stroll south to Kaatsbaan Cultural Park, an outdoor performance venue perfect for fresh-air recreation in the off-season. Traghaven is a fun and trendy Irish pub with a serious whiskey selection, while the highly Instagrammable general store has everything you need to picnic by the waters. South of Potts Farm, Jaeger Haus is a traditional German restaurant with a simple interior and casual vibe.

Home to inns and B&Bs, discover what Tivoli can do for you between the art scene and outdoor activities, like a riverside hike or kayaking along the flow. Next to the Tivoli Free Library, Tivoli Bread & Baking is a highly-rated bakery for your morning coffee, while Fortunes Ice Cream is simply unmissable in any weather for the variety and some of the best ice cream you've ever had. Meet friendly animals at the Pony Up Rescue Collective or unwind at Northwind Farm, north of "From the Ground Brewery," with a heap of tap variety and an outdoor area near a lake. Minutes north, the Clermont State Historic Site in Germantown is worth your time on a tour of the circa-1750 mansion, plus 500-acre grounds with hiking trails, gardens, and places to relax against river views.

Wassaic

Despite being truly tiny, you will never feel bored in Wassaic, the last stop on the Meto-North Harlem Line, between your morning coffee at Vitsky Bakery and the popular Lantern Inn for dinner. Home to historic sites, antiques, and a drive-in, Wassaic's knack for arts and crafts, plus the old-timey feel, make it a relic in itself. From the creekside, stroll through the heart to the Wassaic Park just south with a playground, and view some really cool 19th-century charcoal kilns right across the highway to the west. The central Harlem Valley Rail Trail offers Instagram shots that will look like you've been to a bygone era.

Shop at Hunter Bee, which sells everything from fine antiques to quirky oddities, while the Red Country Cottage and 1976 Shasta Camper are the budget stays that will keep you close to it all, while a group can rent out the historic Salvato Mill. Perfect for exploring on a bike ride through the nostalgic breeze, the Wassaic Project is a worthy-of-your-time arts organization. The seasonal Kings Highway Cider Shack offers great ambiance and outdoor eats when you need a break from pedaling.

As much as we love road-tripping on weekends with windows rolled down in the summer and the NY countryside bursting through, escape the craziness of the city by stopping off the beaten path. Oftentimes, it is where you haven't been before that you can recharge, unwind, or inspire. Narrowsburg hides in between the Catskills and the Poconos across the Delaware River from Pennsylvania.