Aerial view of Cooperstown, New York with the water in the background.

12 Coolest Small Towns in New York for a Summer Vacation

New York State is often associated with the bustling city that shares its name. However, beyond the concrete jungle lies a treasure trove of charming small towns, each with its unique character and attractions. These little havens are perfect for a summer vacation, offering a serene retreat from the daily grind. From picturesque lakeside towns to historic hamlets, New York State has something for everyone. The coolest small towns in the Empire State offer beautiful landscapes, outdoor activities, and unforgettable experiences. So pack your bags and get ready to discover the hidden gems of New York State that await you this summer.

Lake Placid

Adirondack chairs by the water in Mirror Lake, Lake Placid New York.
Mirror Lake, Lake Placid, New York.

Nestled in the heart of the Adirondack Mountains, Lake Placid is a haven for outdoor enthusiasts. With the pristine Mirror Lake, visitors can enjoy water activities like kayaking, paddle boarding, and fishing. This charming town is also home to the historic 1980 Winter Olympics venues, including the Olympic Center, where you can still watch sporting events and ice shows. Explore the quaint downtown area filled with unique shops, eateries, and galleries, or take a scenic drive up Whiteface Mountain for breathtaking views of the Adirondacks. With numerous trails for hiking and mountain biking, and wildlife-watching opportunities at the nearby Adirondack Wildlife Refuge, Lake Placid offers a perfect blend of adventure and relaxation.

Cold Spring

People walk along the main shopping district of Cold Spring, New York.
The main shopping district of Cold Spring, New York. Image credit James Kirkikis via Shutterstock

Cold Spring is a quaint riverside village on the banks of the Hudson River. This picturesque town boasts antique shops, art galleries, and waterfront dining options with stunning views of the river. Take a stroll along the river, explore the nearby Hudson Highlands State Park, or catch a glimpse of the imposing West Point Military Academy across the water. History buffs will appreciate the rich history of Cold Spring, with its well-preserved 19th-century buildings and the nearby Boscobel House and Gardens, a beautifully restored neoclassical mansion. Outdoor enthusiasts can hike up to Breakneck Ridge or Bull Hill for panoramic vistas of the Hudson Valley. And, for a unique experience, hop on the Metro-North Hudson Line for a scenic train ride along the river, with stops at other charming Hudson Valley towns.

Skaneateles

Shops, Restaurants and Condominium on Skaneateles Lake, view from the pier, Skaneateles, New York
View from the pier, Skaneateles, New York.

Skaneateles is a picturesque village on the shores of Skaneateles Lake, one of the stunning Finger Lakes. This charming town offers a delightful combination of boutique shops, galleries, and world-class dining, all set against a backdrop of crystal-clear waters and lush green hills. Take a cruise on the lake aboard the Judge Ben Wiles or the Barbara S. Wiles, or rent a kayak or paddleboard to explore the shoreline at your leisure. The Skaneateles area is also home to several wineries, such as Anyela's Vineyards and White Birch Vineyards, where you can sample locally produced wines while enjoying spectacular lake views. If you are visiting in July, make sure to attend the Skaneateles Festival, a month-long celebration of music featuring renowned artists from around the world.

Aurora

Sign of “Long Point Winery”, situated on the east side of Cayuga Lake, known for producing the finest dry red and white wines.
Sign of Long Point Winery overlooking vineyards. Image credit PQK via Shutterstock

Aurora is a serene village situated on the eastern shore of Cayuga Lake, the longest of the Finger Lakes. This idyllic town offers beautiful lakefront views, elegant historic buildings, and the prestigious Wells College. The village is home to several architecturally significant structures, including the Aurora Inn, a luxurious lakeside boutique hotel, and Rowland House, a beautifully restored mansion filled with contemporary art. Spend an afternoon wine tasting at the nearby Long Point Winery or Bet the Farm Winery and enjoy the stunning views of Cayuga Lake. For a leisurely day on the water, rent a boat, kayak, or paddleboard and explore the shoreline, or unwind on the small public beach with a picnic. Nature lovers can hike the numerous trails at the nearby Long Point State Park or visit the Montezuma National Wildlife Refuge, a haven for migratory birds and wildlife. With its rich history and tranquil atmosphere, Aurora is the perfect destination for a relaxing summer vacation.

Woodstock

A store in Woodstock, New York, invokes the spirit of 1969, selling vintage styles and posters of rock stars from the 1960s.
Legends in Woodstock, New York. Image credit James Kirkikis via Shutterstock

Woodstock, famous for the legendary 1969 music festival, is a bohemian town nestled in the Catskill Mountains. With a thriving arts scene, eclectic shops, and a variety of outdoor activities, Woodstock offers the perfect blend of culture and nature for a memorable summer vacation. Explore the town's numerous galleries and studios, such as the Woodstock Byrdcliffe Guild and the Center for Photography at Woodstock. Music lovers can visit the original site of the Woodstock festival at the Bethel Woods Center for the Arts, which now hosts concerts and cultural events. Outdoor enthusiasts will enjoy hiking or mountain biking in the nearby Catskill Forest Preserve or kayaking on the scenic Ashokan Reservoir. For a unique experience, visit the Karma Triyana Dharmachakra, a Tibetan Buddhist monastery that offers meditation classes and spiritual teachings.

Cooperstown

US Flag in the middle of the street and lush green trees frame the Main Street in Cooperstown, New York
Main Street in Cooperstown, New York. Image credit Ritu Manoj Jethani via Shutterstock 

Home to the National Baseball Hall of Fame and Museum, Cooperstown is a must-visit for sports enthusiasts. Located on the southern tip of Otsego Lake, this historic town offers picturesque views, waterfront activities, and plenty of family-friendly attractions. Discover the story of America's favorite pastime at the Hall of Fame, or take a guided tour of the Fenimore Art Museum, which houses an extensive collection of American folk art and Native American artifacts. For a dose of nature, rent a boat or kayak and explore the pristine waters of Otsego Lake, or hike the nearby Glimmerglass State Park. Beer lovers will appreciate a visit to the Brewery Ommegang, a Belgian-style brewery offering tastings and tours. Whether you are a baseball fan, a history buff, or an outdoor adventurer, Cooperstown has something for everyone.

Greenport

Sunrise at the Mitchell marina of Greenport Village, Long Island, New York
Mitchell Marina of Greenport Village, Long Island, New York.

Greenport is a vibrant coastal village on the North Fork of Long Island, overlooking Shelter Island. The town boasts a rich maritime history, charming shops, and an array of seafood restaurants serving fresh, locally caught fare. Stroll along the harbor and admire the historic Carousel, or visit the East End Seaport Museum to learn about the area's maritime heritage. Relax on the nearby beaches, such as Orient Beach State Park, or take a scenic tour of the local vineyards and wineries, including Kontokosta Winery and One Woman Wines & Vineyards. Greenport is also the gateway to Shelter Island, a tranquil retreat accessible by ferry, where you can explore the Mashomack Preserve, a 2,039-acre nature reserve with miles of hiking trails and stunning coastal views. Greenport offers a quintessential Long Island experience, combining history, nature, and maritime charm.

Lewiston

Lewiston, New York as seen from the dock on the Niagara River, with Queenston, Ontario, Canada in the background.
Lewiston, New York, as seen from the dock on the Niagara River. Image credit Atomazul via Shutterstock

Just a stone's throw from Niagara Falls, Lewiston is a quaint village on the banks of the Niagara River. This charming town is steeped in history, with attractions such as the Lewiston Museum and the Freedom Crossing Monument, which commemorates the town's role in the Underground Railroad. Take a leisurely stroll down Center Street, lined with unique shops, galleries, and eateries, or enjoy live music at local venues like the Brickyard Brewing Company or Artpark, an outdoor amphitheater that hosts concerts and theatrical performances. For a taste of the region's natural beauty, visit the nearby Niagara Falls State Park or embark on a thrilling jet boat tour of the Niagara River with Niagara Jet Adventures. Foodies will love the delicious farm-to-table fare at the town's charming restaurants, such as Carmelo's and The Silo. With its rich history, stunning riverside views, and proximity to Niagara Falls, Lewiston is a delightful destination for a summer vacation.

Watkins Glen

Picturesque view from the iconic Pier House at Watkins Glen.
Pier House at Watkins Glen.

Famous for its breathtaking gorge and waterfalls, Watkins Glen is a nature lover's paradise. Situated at the southern tip of Seneca Lake, the largest of the Finger Lakes, the town offers a range of outdoor activities, including hiking, boating, and wine tasting. Explore the scenic Watkins Glen State Park, with its 19 waterfalls and picturesque gorge trail, or take a leisurely walk around the harbor and marina. The town is also home to the Watkins Glen International, a renowned race track that hosts NASCAR events and other auto races. For a taste of the region's viticulture, visit the Seneca Lake Wine Trail, featuring over 30 wineries, such as Castel Grisch Winery and Lakewood Vineyards. Whether you are an adventure-seeker, a wine connoisseur, or looking for a scenic escape, Watkins Glen is an ideal destination.

Rhinebeck

Crowds of visitors at the Dutchess County Fair, Rhinebeck, New York
Dutchess County Fair, Rhinebeck, New York. Image credit Alexanderstock23 via Shutterstock

Rhinebeck is a picturesque village in the Hudson Valley, boasting beautifully preserved historic homes, tree-lined streets, and charming shops. Explore the nearby Dutchess County Fairgrounds, which hosts the annual Dutchess County Fair and other events throughout the year, or visit the Old Rhinebeck Aerodrome, an aviation museum with vintage aircraft and thrilling airshows. Take a scenic cruise on the Hudson River with Hudson River Cruises, or enjoy a leisurely walk through the picturesque Poets' Walk Park. History enthusiasts will appreciate a visit to the nearby Vanderbilt Mansion, a Gilded Age estate set on 211 acres of parkland, or the Staatsburgh State Historic Site, a lavish Beaux-Arts mansion overlooking the Hudson River. With its rich history, beautiful landscapes, and small-town charm, Rhinebeck is a delightful destination for a summer vacation.

Saranac Lake

A dock and lamp post on a cloudy afternoon in the Adirondacks on Lake Flower at Saranac Lake, New York
Lake Flower at Saranac Lake, New York.

Located in Adirondack Park, Saranac Lake is a vibrant, artsy town surrounded by stunning wilderness. The town is known for its thriving arts scene, with galleries like the Adirondack Artists Guild and the BluSeed Studios showcasing local talent. Outdoor enthusiasts can enjoy canoeing, kayaking, or paddleboarding on the beautiful Saranac Lake chain or explore the numerous hiking and biking trails in the surrounding mountains. For a unique experience, visit the historic Saranac Laboratory Museum, which played a pivotal role in tuberculosis research during the early 20th century. In the winter, the town hosts the annual Saranac Lake Winter Carnival, a 10-day festival featuring ice sculptures, parades, and fireworks. With its lively arts and culture scene, abundant outdoor activities, and breathtaking mountain views, Saranac Lake is a perfect destination for a summer vacation.

Sleepy Hollow

A scenic look along the Hudson River shoreline in the village of Sleepy Hollow in New York state.
Shoreline in the village of Sleepy Hollow in New York state. Image credit Andrew F. Kazmierski via Shutterstock

Sleepy Hollow, located on the east bank of the Hudson River, is famous for Washington Irving's legendary short story, "The Legend of Sleepy Hollow." This historic village offers a unique blend of culture and history, with attractions like the Sleepy Hollow Cemetery, where you can visit the graves of Washington Irving and other notable figures. Explore the nearby Philipsburg Manor, a restored 18th-century mill and farm, which offers a glimpse into the lives of early Dutch settlers. Discover the Kykuit, the Rockefeller Estate, a stunning Beaux-Arts mansion set amidst expansive gardens and terraced lawns, offering panoramic views of the Hudson River. For outdoor enthusiasts, take a hike in the Rockefeller State Park Preserve, with its 45 miles of carriage roads and picturesque woodlands. In October, the town comes alive with Halloween-themed events, such as the Great Jack O'Lantern Blaze, featuring thousands of hand-carved illuminated pumpkins. With its rich literary history, fascinating historic sites, and stunning river views, Sleepy Hollow is a captivating destination for a summer vacation.

New York State's small towns offer a wealth of hidden gems waiting to discover. Whether you are seeking outdoor adventure, historical sites, or a peaceful retreat, these enchanting towns are perfect for your next summer vacation. So why not escape the hustle and bustle of city life and experience the charm and allure of these delightful destinations?

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