Last Updated on: 18th March 2023, 11:07 pm
When you’re looking for a place to get away to, often a big city is appealing, but other times you just want to relax and soak up the ambiance and history of a small town. These are the best historic small towns in New York for you to unwind in and enjoy.
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My Favorite Travel Booking Sites for 2023
These are my favorite companies that I use on my own travels.
Protect Your Trip via Safety Wing
Find the best city tours, day tours, bus tours, & skip-the-line tickets on GetYourGuide and Viator.
Find the best deals on hotels & vacation rentals on Booking.com.
For English-speaking private airport transfers, book through Welcome Pickups.
For road trips and independent travel, rent a car through Discover Cars.
Find information and cruise reviews on Cruise Critic.
For packing and travel essentials order via Amazon.
Book an affordable family or romantic photography session on your trip through Flytographer (Use the code HISTORYFANGIRL for 10% off your first photoshoot).
For travel guidebooks to have with you during your trip, I always pick one or two from Rick Steves and Lonely Planet.
The Best Historic Small Towns in New York
In no particular order…
A beautiful town in the southern Fingerlakes, Corning is home to some fabulous museums, making this a great place to escape to if you want to get a little arts and culture into your itinerary.
The Corning Museum of Glass is home to the largest collection of glassworks in the world, and the institution is dedicated to the preservation and study of glassmaking. They even have a glassblowing school.
If you’re looking for a historic New York town to enjoy an idyllic weekend in, then a visit to the Rockwell Museum is a perfect fit. Nothing says “historic Americana” like a Norman Rockwell painting!
Founded in 1796, you’ll find historic spots here that date back to the early days of the country. Make sure to set aside some time to explore Corning’s Gaffer District. You can use this free self-walking tour to learn all about the district’s history.
Any town that figures in a Washington Irving tale has a place in the New York history books, but if you want to know which one to visit I’d suggest starting with Sleepy Hollow.
The eponymous tale is a spooky delight, making Sleepy Hollow the perfect town to run away to for a History Lovers out there. You can celebrate Halloween (or any day in October) at the Great Jack O’Lantern Blaze, which features over 7,000 Jack O’Lanterns!
The best place to learn about the legend of Sleepy Hollow in on a tour of the local cemetery. They even have a version with cocktails!
If you want to learn more about Washington Irving, he lived in nearby Tarrytown. You can tour or visit many of the places associated with his life and works.
Founded in the 17th century, the town is part of the area of the Hudson Valley taken by Dutch Settlers fighting against the Weckquaesgeck tribe. The first time the area appeared on a Dutch map was in 1655.
The Thousand Islands region of Canada and New York is less famous in the states than the Hudson Valley or the Finger Lakes, but this charming region is full of historic sites to explore!
For historic sites, it doesn’t get much better than Boldt Castle, one of the only castles in America (and one of the prettiest castles in the world). You can also tour Singer Castle, which is smaller but just as lovely.
Nautical enthusiasts should make sure to check out the Antique Boat Museum, which features over three hundred historic boats.
One of my personal favorite historic New York towns, Montauk is the perfect combination of a beach destination, foodie heaven, and place for history lovers.
After spending a few days on the beach and eating your fill of lobster rolls at the best roadside stands, you can start to learn about the area. The first place you should go is the Montauk Point Lighthouse, which is more than just a pretty Instagram spot. It’s also a National Historic Site.
If you want to go to the top of the lighthouse, you’ll find 137 steps are separating you from that spectacular view at the top. They’re well worth it, in my opinion!
If you like your history on the bougie side, enjoy a meal and a stroll at the Montauk Yacht Club, which was founded in the 1930s, has been newly renovated. You can also stay right on their water, though it will cost you a pretty penny.
It was this yacht club that took Montauk from a sleepy fishing village into one of the most popular getaways from New York City, so even a day at their spa counts as enjoying a slice of local history.
If you want to enjoy a few days in the Adirondacks, head to Lake Placid. Boasting the slogan “America’s First Winter Resort.” Rich New Yorkers have been vacationing here since the late 1800s, but it was hosting the 1932 and 1980 Winter Olympic Games that truly put Lake Placid on the map.
You can learn about the history of these events at the Lake Placid Olympic Center Museum, or you can a more hands-on experience with an Olympic Site Pass at the Lake Placid Olympic Village. Feeling lucky? Try your hand at the Lake Placid Olympic Bobsled Experience.
Set aside some time to shop in the village’s quaint downtown.
The namesake music festival isn’t the only history tiny Woodstock boasts, though you can certainly indulge in it while you’re here! Outside of town, you can visit the field where the festival was held as well as visiting the Museum at Bethel Woods.
Even if you aren’t interested in music history, you can (and should!) enjoy a few days in town. There’s a lovely charming-meets-hippy vibe with lots of local shops to peruse as you walk around and explore.
Make sure to check out Wagwear, the second location of this local NY upscale dog clothing boutique. It’s one of my favorite New York souvenirs!
Home of the 1848 Seneca Falls Convention, this town belongs on every women’s history bucket list. You can explore this at the Women’s Rights National Historic Site in town, as well as paying a visit to the Women’s Hall of Fame.
Of course, there’s a kitschier reason to visit as well, and that’s to check out the It’s a Wonderful Life Museum dedicated to the film.
It doesn’t hurt that this much history is packed into such an idyllic setting! You can easily spend a long weekend here soaking up the atmosphere while learning about the town’s important role in American history.
Famous as the site of the Baseball Hall of Fame, there’s more to historic Coopertown than balls and bats. Known as “America’s Most Perfect Village,” Cooperstown has a Stars Hollow vibe perfect for soaking up the small-town mood.
If you want to know what life was like in upstate New York in the nineteenth century, head to the Farmers’ Museum, a living history museum where you can immerse yourself in rural life.
This beautiful village in the Finger Lakes is a beautiful supper escape and a great place to enjoy the Finger Lakes Wine Trail. Dating back to the 1830s, the town boasts a beautiful lakeside church that would make any Instagrammer flip their lid.
Skaneateles is a great winter destination. You can enjoy the town’s Dickens Christmas celebration each weekend in December. Think New York meets a Christmas Carol. The end of January is a great time to visit as well when you can experience the town’s Winterfest.
Just a stone-throw from NYC, Oyster Bay is a collection of charming hamlets on Long Island. It’s so close that it was originally a part of Queens. Yet when you get here, you feel like you’re in another world.
While here, check out Teddy Roosevelt’s “Summer Whitehouse” which has been turned into a museum, as well as the Seawanhaka Corinthian Yacht Club, which is one of the oldest yacht clubs in the Americas.
Dating back to 1789, Ithaca might be one of the country’s most famous university towns, but it’s so much more than just a place to party!
I love visiting the large Ithaca Farmers Market on the weekend. You can try the local wine, farmstead cheese, and check out their live music performances.
You’ll also want to spend some time in Ithaca Commons, a lovely pedestrian-only area downtown where you can brunch, sip cocktails, and shop until you drop.
You can stroll Cornell Campus to soak in the beautiful architecture, but its the area’s state parks, waterfalls, and gorges that are the biggest draw. This rock climber’s paradise is perfect for anyone who wants to mix history, culture, and adventure travel.
Dating back to 1802, Saranac is another unspoiled Adirondacks hamlet that makes for a great getaway year-round. You can take it all in on this historic walking tour which covers the town’s history while walking allowing you to enjoy the town’s gorgeous lake and river setting.
If you like a bit of the macabre, you can check out the Charles Dickert Memorial Wildlife Museum, which features over one hundred pieces of taxidermy.
Literature and history lovers can check out the Robert Louis Stevenson Cottage and the Six Nations Indian Museum.
The largest town on this list, Rochester is not really a town. It’s the third-largest city in New York. But it’s a great place to stay to access Genesee Country Village & Museum, which is a working 19th-century village.
You can visit the Pioneer Center and see what life was like here for the earliest European settlers at the end of the eighteenth century, see what the village had become by the 1830s, and learn all about how New York changed in the years after the Civil War as modern technology shaped the town.
During the day, immerse yourself in pastoral New York life and come back to Rochester at night to enjoy a more urban vibe (and the accompanying amenities).
5 Things to Pack for Your Trip to New York
The Lonely Planet New York guidebook. It can be kind of a pain to find the major guidebooks once you land, or you’ll find them overpriced. I always like to pick mine up ahead of time.
An Unlocked Cell Phone so that you can use a local sim card while here to help navigate public transportation and when you’re on the road. (For people without American cell phone plans).
Backup Charging Bank for your cell phone since you’ll be using it as a camera, GPS, and general travel genie.
A Camera since New York is super photogenic. I use a mix of my Nikon D810 and my Samsung8 smartphone these days.
A Great Day Bag so you can carry what you need with you (like your camera, snacks, water, sunscreen, cash, etc). My current favorite is the Pacsafe Citysafe, which is especially great for New York because it has many anti-theft features designed to deter pickpockets. It also transitions to a night bag more easily and won’t embarrass you if you go to dinner directly after sightseeing all day.
More New York Travel Resources
If you live in New York City and are looking to escape for a few days, check out my guide to renting a car in NYC,
If you know you’ll be putting Niagara Falls on your itinerary, check out One Perfect Day in Niagara Falls, what to buy in Niagara Falls, the best Niagara Falls quotes, and Niagara Falls puns.
Don’t Forget About Travel Insurance!
Before you leave for New York make sure you have a valid Travel Insurance Policy because accidents happen on the road. I pay for World Nomads, and I happily recommend them. It’s especially important to get travel insurance if you’ll be hanging enjoying time in the beautiful (but occasionally slippery) outdoors.
I have been a paying customer of World Nomads for travel insurance for three years, and I happily recommend them. If you get sick, injured, or have your stuff stolen, you’ll be happy to have the ability to pay for your medical bills or replace what’s stolen or broken.