8 Of The Friendliest Little Towns In New York

New York can be associated with many things, yet "friendly" is rarely the first word that springs into mind at the mention of the Empire. Not to say that it isn't, but the facts are facts, and there is American tourist solidarity in regards to friendly places, and New York wasn't even in the top 10 states (according to the World Population Review 2023 poll). Spoiler alert: Minnesota came first.

If there is anything NY towns can do, it is charm up the visitors. Just think of Skaneateles, although a larger town. Visit Westfield on a Great Lake for water fun, boating, and atmospheric sunset strolls, then steer clear of the Hamptons in Greenport for a seaside escape. Each with a fun upcoming festival, like Saugertie's quirky Hudson Valley Garlic Festival, offers to relax and recharge.

Chittenango

The natives knew the area as "Where waters run North" or Chu-de-naag, their name for the Oneida's creek. Today, Chittenango is most famous as the birthplace of L. Frank Baum, the author's children's classic “The Wonderful Wizard of Oz.” Younger parents associate it with the popular Oz-Stravaganza, while the adventurous picture is of the beautiful waterfall at Chittenango Falls State Park. The amiable town, central in the Empire, is like its kind heart. Offering easy access to whatever holds the most appeal, maybe it's the All Things Oz Museum, which hosts the annual celebration and honors Baum's timeless tale that exudes magic for young and old alike.

Families enjoy the original props and costumes from movies and musicals, Judy Garland's autograph, and rare collectibles. For goodwill gambling, Yellow Brick Road Casino & Sports Book features slots and table games, plus bowling, mini golf, and plentiful dining for the whole gang to have fun. Sullivan Park is a dog-friendly woodland, while Green Lakes State Park has a swimming lake, plus a golf and ski center to the west. Chittenango Landing Canal Boat Museum offers up the intriguing story behind the historic canal, which is not far from the canoe boat launch in town. After a stroll to Chittenango Creek Erie Canal Aqueduct, drop by Nina’s Pizza & Italian Restaurant for pizza and wings.

Greenport

For a memorable seaside getaway, Greenport is snug on the North Fork of Long Island Sound. The friendly "East End" town can be adventurous, peaceful, or full of family-fun discoveries. Overlooking Gardiners Bay to the east, if you squint, Long Beach Bar Lighthouse winks back. Enjoy a picnic at Inlet Pond County Park after a stop at the local farmer’s market in Mitchell Park. Many come to feast on fresh seafood, yet others know of the area's viticulture, with over 40 wineries and verdant vineyards. East End Seaport Museum & Marine Foundation hosts the annual Maritime Festival in early fall. The lively and picturesque waterfront packs a mile-long square.

Drop by Kontokosta Winery or Billy's by the Bay, among other seafood stops, boutiques, breweries, and antique haunts. Families enjoy ice cream shops and attractions like Camera Obscura, Greenport Village Blacksmith, and, most of all, the carousel on the Greenport Harbor side of town. The area is rife with maritime history and views like those from the 67 Steps Beach or aboard Rast End Charters. From shopping to a beach and idyllic nature slices, the Village of Greenport Mccann is a central and top-rated, dog-friendly campground. Claudio's offers a laid-back terrace, while Little Creek Oyster Farm & Market serves shucked oysters and local beers in a harborside cottage with outdoor seating.

Greenwich

Greenwich is a friendly town on the Battenkill River, which unites with the Hudson to the west. The area is defined by rolling hills and powerful waterfalls. Witches Village Cafe serves a delicious breakfast in a red building by the river bend. Grab a latte for a stroll along Salem Street or the dog-friendly Dionondahowa Falls Trail to a large waterfall in autumnal colors. Stay for the unique celebration of Panama’s independence from Colombia (1903) on November 3. Surrounded by farms and farmers' markets, chat up with the friendly owners in the warmer months. Carters Pond Wildlife Management Area offers hiking and birdwatching alongside Denton Sanctuary and Livingston Brook Preserve.

From the waterfront Greenwich Recreation Park to great fishing and canoeing along the river, nature disperses to explore on a sunny hike or hide in the shade. For those who love covered bridges, there are three storybook-red in the area, including the historic Raleigh, Eagleville, and Arlington-covered bridges. End the night over a flight at Argyle Brewing Company. The locals come out to play in winter, ice skate in the village, plus sledding hills and snowmobiling in the open fields. Washington County Fair Farm Museum displays life between the 1800s and the 1940s with artifacts, and Saratoga Monument is just 13 minutes west of Schuylerville. Don't miss the Ice Cream Man on the way.

Narrowsburg

Within the Town of Tusten, the charming hamlet of Narrowsburg is defined by glittering blue water and green fields across the Delaware River from Pennsylvania. The name nods at the cozy spot along the river, which snakes over and west of town, centered in the Upper Delaware River corridor. Surrounded by water on two sides, there are verdant rolling hills transitioning into the towering oaks and evergreen forests in the foothills of the Catskill Mountains. Once a thriving logging town, the hikers enjoy the all-around rural western Sullivan Catskills charm. From riverside strolls to a network of trails, canoeists, kayakers, and rafters flock to the area's pristine waters of the Delaware.

Tusten Mountain Trail offers spectacular river views, while the friendly residents of the area include whitetail deer, black bears, blue herons, and bald eagles. Many enjoy rafting tours with Lander's River Trips, an outfitter down the road, alongside the fishing charters to catch shad, trout, smallmouth bass, and walleye. From the Delaware Valley Arts Alliance to the Delaware Valley Opera and the Tusten Theatre, the festivals along the Main attract summertime crowds, including Riverfest, a traditional art fair. Narrowsburg also serves as the center point to explore Route 97 Scenic Byway, so when you come for the family-friendly Honey Bee Fest, take a relaxing drive with views that are easy on your eyes.

Rhinebeck

Once a hip Hudson Valley retreat for weekenders, now a classy arts destination, Rhinebeck keeps up the historic allure. Beekman Arms Inn is America's oldest inn, while the Wilderstein Historic Site offers tours of the 19th-century ornate Queen Anne mansion on 40 riverfront acres. Dutchess County Fairgrounds hosts hot air balloon shows and bookable rides to see the valley from above—an unforgettable family or romantic pursuit. With its deep appreciation for performing arts, visitors can enjoy great music, dance, live theater acts, plus independent films. The antique (1900-1935) airplanes at Old Rhinebeck Aerodrome still fly in shows.

Across the Hudson River from Kingston, which few know was the state's first capital city, Rhinebeck has the bucolic charm of New York's scenic Hudson Valley that draws outdoor enthusiasts. From kayaking and fishing along the river to the iconic Ferncliff Forest trails, pack a picnic for Drayton Grant Park at Burger Hill. It is hard to take your eyes away from the real estate envy, the Victorian homes of the Hudson River Historic Landmark District, in the warm glow of sunset. Vlei Marsh is a kid- and dog-friendly hike, while Trail Poets' Walk Park is another nod to the town's artistic energy, with a scenic gazebo and beautiful riverside trails for intimate strolls.

Saugerties

Saugerties hones a sweet spot between the Catskills and Adirondacks on the Hudson River's eastern bank. Saugerties is a picture-book-perfect mountain retreat for a memorable family getaway in any season. Whether you're coming for lush hikes or the falltime splendor, the incredibly scenic surroundings need no sugar-coating. Diamond Mills Resort & Spa is a beautiful historic residence on the doorstep of Saugerties Village Beach, a dog-friendly spot to relax and stroll down to the marina at sunset. From the verdant Seamon Park with pretty features to ice-skating year-round at Cantine Field, browse the trendy Partition Street's unique storefronts, pop-ups, and restaurants.

From Josi's Coffee Shop in the morning to lunch at the Village Diner, try garlic-flavored ice cream during the town's quirky Hudson Valley Garlic Festival. The charming Saugerties Lighthouse is an icon that doubles as a friendly accommodation in a real slice of history with the best views over the river. If you take out a kayak or paddleboard on Esopus Creek, visit the Esopus Bend Nature Preserve. Between the cinema and Emerge Gallery & Art Space on Main, the Dutch pours 16 draft beers, with a focus on local ingredients in a restored tavern. Right across the river, Clermont State Historic Site offers tours of the circa-1750 mansion with gardens, plus trails and river views on 500 acres.

Westfield

Westfield is a gem on Lake Erie's south-central shore. Barcelona is its friendly lakefront neighborhood, with camping and lakeside spots to relax in views of the 1800s Barcelona Lighthouse, a cool stony face at the top of a hill near the fishing and boating pier. Private Paradise is a protruding, serene beachfront, not to be confused with the main Barcelona Harbor Beach. From fishing to sailing and water skiing, venture back into town for dinner at Parkview Restaurant. The nearby McClurg Museum/Chautauqua County Historical Society is next to the popular Westfield Village Antique Center. With Chautauqua Creek through the heart, it is minutes inland to Chautauqua Lake.

Westfield is at the heart of the world’s largest Concord Grape Belt for those looking to combine adventures and relaxation. Surrounded by farms and wineries with year-round tours and tastings, Lake Erie Grape Discovery Center is the official Visitors Center for the Grape Belt. Pick up a bottle from Mazza Chautauqua Cellars. And what's better than complementing viticulture with more culture over a concert, theater, or dance performance? Don't miss Portage Pie any day for a casual bite while the YWCA Arts & Crafts Festival fills the downtown park with art, crafts, and food annually in July. Art fans can also visit the iconic Chautauqua Institution, which is minutes away and has a deep history and summer programming.

Windham

Established in 1798, Windham is one of the region's oldest towns. In direct views of Windham Mountain, explore the quaint and charming downtown for a deeply historical insight. The “gem of the Catskills” paints its over two-century-long story along the historic Main with shops, cafes, and boutiques that will take your breath away on a stroll. The locally owned restaurants serve hearty Catskills meals with claims to be world-class. Chicken Run Family Restaurant and Steak House is a staple with a casual feel, full bar, and regular live music. Under the watchful eye of the dominating peak and Batavia Kill through the heart, Tubing Park is a family hotspot.

Tangled amid mountain bike and hiking trails, the Windham Path is a dog-friendly hiking area with open views, while Windham Mountain Club is a ski resort. Things can take a quirky turn if you book an hour at Magic On Main, a local attraction. Hidden in the Catskills, the often-overlooked town in western New York is actually very well connected, under an hour east of Albany and the tri-state wilderness crossroads to the west. Windham offers fantastic lodgings at fair prices, like Christman's Windham House, among charming B&Bs, inns, and other resorts, plus a golf course. Drop by Windham's 31st Annual Autumn Affair on Columbus Day weekend in October.

Embracing the Warmth of New York's Friendliest Towns

Tourism highly depends on the friendly vibes in a town or city. In Rhinebeck, visitors can enjoy great music, dance, and live theater acts, surrounded by the splendor of New York's scenic Hudson Valley. Visit Chittenango for Oz-Stravaganza, June 6-8, and pretty falls at Chittenango Falls State Park.

Narrowsburg boasts a wildlife-rich area with amiable creatures like whitetail deer, blue herons, and bald eagles. NY's tiniest towns will make you forgive and forget its fast-paced lifestyle and aggressive drivers. Pick any of these friendly gems on a fun or relaxing getaway to recharge for life back home.