The Most Charming Small Towns In New York You Have To Visit.

Finger Lakes New York flags on houses

New York is far more than just the city, and this small selection of charming towns and villages in New York State will hopefully show you that the entire region of New York is an incredibly underrated destination that is well worth taking the time to discover!

New York City is an incredible destination, there is no denying that. It does however unfortunately overshadow its upstate neighbours quite a lot and I want to show you all that there is a lot more to New York than just New York! This huge and beautifully stunning state, from the lakes and waterfalls of the Finger Lakes Region to the small town charm of the Catskills and the Hamptons, there are plenty of smaller regions within New York that simply ooze small town charm and picturesque scenery. So here are just some of my favourite charming small towns in New York state that you have to visit!


Known as America’s crystal city, this charming town is the perfect escape from the hustle and bustle of NYC. The town square is regualarly noted as one of Americas most beautiful and the dozens of boutique shops, art galleries and local restaurants have earned its historic Market Street a number of awards and accolades too. Corning’s unique tourism offering centres around all things glass, celebrating its unique industrial heritage after making the very first lightbulb for Thomas Eddison. Check out the Corning Museum of Glass for artisan glass and crystal, and if you can visit during May when they hold the GlassFest or in the Autumn during the 100 Days of Incandescence where the whole town is transformed into a light filled parade. If you want a taste of small town America, this is a perfect option.


Located in the heart of the Finger Lakes, Ithaca is often called the most beautiful town in New York, with the town itself filled with neoclassical landmarks like the famous Ivy League Cornell University and surrounded by the famous Ithaca Waterfalls. There are well over 150 forested waterfalls surrounding this delightful little town, all fed from the pleasant Cayuga lake, and that alone makes spending some time here worth it. Even if you don’t take the time to hike the many trails including the six mile creek and Cascadilla Gorge, and why wouldn’t you, you can sit and admire the views from many of the towns local eateries, restaurants, boutique hotels and viewing spots.


Yes, I’m talking about that Woodstock! The Woodstock! This picturesque small town in the Catskills is famous for the legendary music festival in 1969, nevermind the fact that the festival was actually held in a field in Bethel a short drive away, the town of Woodstock still celebrates that musical heritage with a bohemian feel, endless art galleries and boutiques, music and film festivals and independent shops and restaurants filled with Woodstock memorabilia. They even have a Buddhist monastary here! Beside that the town itself is quintessentially small town American with picturesque architecture and flags galore, all surrounded by stunning mountain and countryside views.


This charming little town in Western New York is celebrated as New York’s playground for outdoor fun and adventure, and people descend on this small town for the opportunity to go hiking, fishing, paddle boarding, kayaking and even skiing and mountain biking! The pristine mountain backdrop enhances the small town feel of Ellicottville which is enjoyed through sampling any one of its plethora of amazing independent restaurants, boutique shops, craft beer scene or attractions like the picturesque Griffis Sculpture Park.


Located on the beautiful Seneca Lake in Finger Lakes, where quite fraankly it is difficult to find anywhere that isn’t extremely picturesque, Geneva is surrounded by the stunning Seneca Lake Park which is a haven for those looking for a lazy weekend of easy watersports and hiking, but it is the beautifully historic architecture that Geneva is really known for. The distinctive neoclassical rowhouses are highlighted by the uniquely art deco and baroque Smith Opera House and Rose Hill Mansion, as well as the stately Belhurst Castle dating back to 1880.


I just love saying Montauk! Even the name is charming! This charming town in the Hamptons, situated at the most easterly point on Long Island, is typically Americana and gave me a distinctive Goonies feel with its famous lighthouse, waves crashing against the pier and dramatic cliffside views. It is also extremely laid back as a town and is a great place to come and surf, relax on the beach and eat some amazing fresh sea food from the numerous food trucks.

Bemus Point.

ships docked at a harbour in Finger Lakes New York

Bemus Point, a small but infinitely charming town on the shores of Chautauqua Lake, showcases this perfectly. It has taken the idea of lake life and run with it to the extent that it is a vital part of the towns identity.

A small boat museum explores the town’s heritage of being on the water and explains why it is such a big part of Bemus Point’s identity with a large portion of the residents owning or using boats in some way, floating festivals on the lake and a common weekend pastime of taking a boat out on the lake to swim and relax; but it is wandering around the town itself, with its quaint, hipster stores, seaside feel and seafood restaurants on wooden docks overlooking the water that really draws you into a sedate way of life that makes you never want to leave!

Watkins Glen.

Home to the famous Watkins Glen International Racing Track, a legendary site in American racing and NASCAR, Watkins Glen still benefits from the astounding beauty of the Finger Lakes region with Watkins Glen state park surrounding the town, Watkins Glen itself can sometimes suffer a little bit from a lack of attention, which is a huge mistake. This underrated but extremely picturesque town is home to a harbour on the edge of Seneca Lake that has unrivalled views over the water and is a perfect place to relax with a glass of wine or a good meal under a covered deck, and row after row of boutique shops, art galleries, locally focused museums and countless independent restaurants and eateries.


Tarrytown is a likeable little town in the Hudson Valley that has a lot of endearing qualities, but the reason it is famous is the village of Sleepy Hollow. I don’t even need to mention the famous Legend of Sleepy Hollow and the works of Washington Irving to tell you why this little village is so well known, and the town really puts out all the stops at Halloween when the tales of Ichabod Crane and the Headless Horseman are brought to life in grand fashion in celebrations that rival NYC at New Year! You can even visit Washington Irving’s estate and the bridge named after one of his most famous characters.


Jamestown is a small town that has a rich cultural heritage of comedy, and that is something that can be found on almost every corner of this New York state landmark.

With a museum dedicated to I Love Lucy and the National Comedy Center supported by comedy greats like Dan Akroyd and Jerry Seinfeld, Jamestown in upstate New York’s Southern Tier is reinventing itself as a comedy mecca for fans, tourists and travellers from all over the world, and is developing an entire tourism industry based around all things funny, and that just adds to the small town charm of Jamestown.


If you are a fan of Huckleberry Finn you will love Elmira! Elmira in the Finger Lakes region is an infinitely lovely town, with quaint neoclassical architecture and a rich history that drew the famous American Writer Mark Twain and was the inspiration for many of his most famous works, a fact that led to the town being affectionately nicknamed Mark Twain Country. You can hop on the pleasantly old fashioned Mark Twain Trolley that will take you on a tour of literary landmarks including his final resting place at Woodlawn Cemetery. But Mark Twain isn’t the only thing this artistic, bohemian town is known for, the unique mix of Italianate and Greek and Colonial Revival architecture gives it a unique character unlike anywhere else in New York.

American flags on houses at Finger Lakes New York

I hope this has helped you realise that New York is far, far more than just the city and that New York state is an incredibly underrated destination that is well worth taking the time to discover for yourself.

Did you enjoy this article? I would love to hear your thoughts in the comments section below or on my Facebook or Twitter pages and please feel free to share it with any or all of the social media buttons. If you want to get more great backpacking tips, advice and inspiration, please subscribe to updates via email in the box to your right.

5 Free Things To Do In New York.

A Day Of Giving Back In Finger Lakes, New York.

New York State.

The Rise Of Comedy Tourism In Jamestown, New York.

There’s More To New York Than The City In Finger Lakes.

Michael Huxley is a published author, professional adventurer and founder of the travel website, Bemused Backpacker. He has spent the last twenty years travelling to over 100 countries on almost every continent, slowly building Bemused Backpacker into a successful business after leaving a former career in emergency nursing and travel medicine, and continues to travel the world on numerous adventures every year.

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Hi, I'm Michael! I'm a former nurse turned published author and world travelling professional adventurer! I have spent over twenty years travelling over 100 countries and I want to inspire you to do the same! Want to know more about me? Just click here!

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