As a midwest transplant, I will never be over Fall on the East Coast, there’s just nothing like it! While I adore New York City in the Fall, it’s also the perfect time to escape for a quick weekend trip to relax and unwind. Every Fall I make it a priority to get out of town to explore a nearby destination. Being in the Northeast I feel so lucky that I don’t have to travel far for a change in scenery. If you’re looking to take a break from the grind of New York City, I’m rounding up some of my favorite weekend getaways from NYC that will leave you feeling relaxed and refreshed! Whether you want to travel by plane, train, or automobile I’ve got your covered with these ideas for 15 weekend trips from NYC!
15 FALL WEEKEND TRIPS FROM NYC
Weekend Getaways from NYC With Friends
Woodstock, New York
Woodstock, New York is one of the cutest little towns in upstate New York and just about a two hour drive from the city. In fact, Woodstock is home to lots of charming local restaurants, live music, shops, and farm stands. You really feel like you’re a world away from the hustle and bustle of New York City! There are tons of Airbnbs in the area making it a great place to book a home with friends for a weekend getaway. Woodstock is lovely all year round, but in the fall when the leaves are changing and there’s a chill in the air it’s particularly magical.
Last fall I visited the Berkshires for the first time and absolutely fell in love! This region in western Massachusetts is filled with farm stands, cozy restaurants, and amazing fall colors if you time your visit right. It’s about a three hour drive from New York City making it super feasible for a quick weekend getaway. I visited with my friend Meghan and we explored the local orchards and farms, did some shopping, and soaked in all the gorgeous foliage. For an extra dose of fall, drive 30 minutes north to Vermont to see even more stunning landscapes!
Visiting the Hudson Valley in the fall is a New Yorker’s rite of passage. Upstate New York is such a special place in the fall! With so many different cities and towns in the Hudson Valley region, I find a car is best if you want to get out and do some exploring. Plus it makes getting around as a group easier, Ubers are hard to come by. From art galleries, to hiking trails, to apple orchards and scenic views of the Hudson River – you can find it all! There are also tons of fabulous farm to table restaurants and cute boutique hotels, making this a great spot for a romantic getaway as well.
The Finger Lakes
This fall I was delighted to visit Steuben County in the Finger Lakes region of New York with my friend Meghan. We had the best time exploring the region’s wineries, restaurants, cute coffee shops, and gorgeous landscapes. It’s a little over four hours driving from New York and truly the most perfect fall destination. I felt like I was in a postcard! I feel like this area is still a little under the radar so visit now before it gets super popular!
For outdoor lovers, another upstate New York region to consider is the Adirondacks. Visit Lake George, Lake Placid, Saranac Lake, or nearby Saratoga Springs and enjoy the many state parks, hiking trails, restaurants, and cute covered bridges. For a fun fall foliage vantage point, take a trip up the Skyride chairlift at the Olympic Jumping Complex in Lake Placid! I think this region is also great for a family getaway.
Weekend Getaways From NYC by Train
Cold Spring, New York
Just an hour and a half train ride from Grand Central Station in New York is the adorable town of Cold Spring. The train actually drops you right off on Main Street so there’s no need for a car at all which is so convenient! There are tons of cute restaurants and some really amazing antique and vintage shops in Cold Spring. You could even make this a day trip with friends if you don’t want to spend an entire weekend!
The train system on the East Coast is unmatched, so I recommend taking advantage of it and hopping on a four hour train ride to Washington, DC! I’ve only visited DC in the spring for Cherry Blossoms but I’ve heard fall is also a great time to visit when the weather cools and the leaves are changing color. For me, a trip to DC always includes delicious food and lots of walking! You can also rent a bike to cruise around the monuments, or bike through Rock Creek Park to admire the fall colors.
Another quick train ride destination is Philadelphia where the cobblestone streets and quaint historic townhomes feel particularly lovely in the fall. This season is a great time to visit and indulge in Philly’s bustling food scene, hang outside at a beer garden with friends, or enjoy cultural offerings like the city’s fall music, film, and comedy festivals.
Luxury Weekend Getaways from NYC
Aurora, New York
A four hour drive from New York City you’ll find the town of Aurora, located on Cayuga Lake in upstate New York. I visited with my friends Allie and Carter and had the loveliest time staying at the luxurious Inns of Aurora. The hotel is actually made up of five different inns, each with its own unique style. The lakeside property has amazing restaurants (we had some incredible meals) and amenities like an onsite spa making it the perfect place for a relaxing weekend getaway. You never even have to leave the property!
Everyone knows The Hamptons and Montauk as a summer getaway spot, but I think it’s lovely in the fall. It’s quieter, easier to get reservations at hotels and restaurants, and just a bit slower pace than in the summer. Plus rentals are usually more affordable! I also suggest checking out North Fork Long Island in the fall (Long Island’s wine country!)
Beach Weekend Getaways from NYC
It’s notoriously difficult (and expensive!) to find lodging on the island of Nantucket in the summer, so I think fall (or even early winter) is the perfect time for a trip. It’s just an hour flight from NYC making it perfect for a quick weekend getaway. I’ve been lucky enough to visit a few times in the summer, but I think visiting Nantucket in the off season is a unique experience as well.
Martha’s Vineyard, Massachusetts
This island off the coast of Massachusetts is a bit bigger than Nantucket and also offers direct flights from New York City. While it’s also an idyllic summer spot, visiting in the fall means less crowds, better priced hotels and rentals, and more (and easier) beach access! I love a bundled up walk along the beach in the fall.
Rockaway Beach, New York
Who said you had to go far for a weekend getaway? Another summer escape that I think can be so lovely on a sunny day in the fall is Rockaway Beach. You can easily get there via subway or ferry from New York City and it feels like a world away!
Where are my Mystic Pizza movie girlies at? You know I had to make a pilgrimage to Mystic, Connecticut with my girlfriends to try the famous titular pizza and it didn’t disappoint! I recommend driving for the easiest access. I love a beach town in the fall, it’s so cozy! All that was missing was Julia Roberts.
Newport, Rhode Island
Just under a four hour drive from New York City is the charming seaside town of Newport. Newport, Rhode Island is the epitome of a coastal New England town and while it’s a big tourist destination in the summer, I think visiting in the offseason can make for a special experience. Stay at the stunning Castle Hill Inn, enjoy a sail if it’s a sunny day, enjoy a stroll along the Cliff Walk, and tour the famous Breakers mansion for some serious interior design inspiration!