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10 Trips to Take from New York City this Fall

It’s that time again. You can feel the slightest chill in the breeze and pumpkin spice is starting to show up on every coffee shop menu. You find yourself itching to wear plaid and wanting to buy cozy sweaters (even though its still 90 degrees in NYC). And all this means one thing: it’s time to start planning fall trips.

I’ve been counting down the days till fall on the east coast since we moved to New York in the spring. I’ve been researching, dreaming and plotting fall trips from New York like it was my job (which hey, it kind of is). I couldn’t take all of these trips this year, despite my best effort, but it seemed like a shame to let my research go to waste.

In this post I’ve rounded up the best trips to take from New York City this fall. We’re talking where to go, what to do, and how to get to 10 of the best fall travel destinations from NYC. And if you’re a New Yorker without a car, this list is for you! Most of these destinations are accessible via public transit.

            Photo evidence that I’ve been a Basic B about fall since at least 2013

Which trip would you take? Or better yet, what destination am I missing? Be sure to let me know in the comments.

For the pumpkin people: Providence, New Jersey

Photo titled Jack-O-Lanterns by under CC BY-NC-ND 2.0

If carving your own pumpkin isn’t enough, maybe you’ll be impressed by the more than 5,000 jack-o-lanterns that line the pumpkin trail at the Roger Williams Park Zoo Jack-O-Lantern Spectacular. This is the fall highlight in Providence, which is only a short 3-hour jaunt from Manhattan.

Before night falls, though, enjoy Providence by day. Take a stroll down Benefit Street, one of the oldest streets in the US, and then meander through the campus of Brown University. Get the best views of the city and the changing leaves at Prospect Terrace park or head down to Waterplace Park.

  • How to get there from NYC: Take the Amtrak Acela or Northeast Regional train from Penn Station to Providence (3 hours)
  • Where to find fall: Roger Williams Park Zoo Jack-O-Lantern Spectacular
  • What you’ll need: Great weather and a free weekend
  • When to go: September 28 – October 31

For the urban foliage folks: Boston, Massachusetts

Photo titled Boston Common by Chase Elliott Clark under CC BY 2.0

Are you outdoorsy, but not that outdoorsy? You want to see the fall leaves, but you don’t want to hike to get there. You can appreciate the crisp autumn air, but mostly just so you can escape it inside a cozy cafe. Get yourself to Boston.

Boston in the fall is everything that’s great about Boston all year, just with even better scenery. Tree-lined streets and pumpkin-covered stoops make even a simple stroll around town feel like magic. Some of the best fall views can be found at Boston Common and Public Garden, two parks right in the heart of the city.

Fill your day exploring the darling Beacon Hill neighbor or walking the Freedom Trail. Relax along the Charles River Esplanade and enjoy a good book on the Commonwealth Avenue Mall. If the Red Sox are doing well, catch some fall baseball at Fenway. No trip to Boston is complete without a cannoli from Mike’s Pastry, but during the full you’re legally required to get the pumpkin variety. (Also try the Boston Creme cake while you’re there, which is also 10/10.)

  • How to get there from NYC: Take the Amtrak Acela or Northeast Regional train from Penn Station to Boston (4 hours)
  • Where to find fall: Public Garden
  • What you’ll need: An equally cozy (and expensive) hotel reservation
  • When to go: Early to Mid October

For the apple pickers: Warwick Valley, New York

It’s not easy to find an apple orchard that’s accessible from New York City without a car. I’m not sure this one technically counts because it does require some rideshare help, but I think it’s about the best you can do.

Apple Ridge Orchards is located just 50 miles outside of New York City. It’s a rustic farm where you can pick your own pumpkins and apples. More importantly, you can purchase fresh apple cider and homemade apple donuts from their farm stand. They also offer hayrides, a petting zoo and a honey bee observation hive.

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  • How to get there from NYC: Take the New Jersey Transit bus #196 from the Port Authority Bus Terminal in NYC to its terminus at Oakland Ave at Orchard St (2 hours). Then use a rideshare service (like Uber or Lyft) to get the final 3.5 miles to orchard (10 minutes).
  • Where to find fall: Apple Ridge Orchards Farm Stand
  • What you’ll need: Cash. Only cash is accepted for admission ($3 per person) and any apples or pumpkins you pick. Food vendors accept credit cards.
  • When to go: September (be sure to check their schedule for Pick-Your-Own availability.)

Planning to be in New York for the holiday season? Consider a visit to the Saks Fifth Avenue Light Show!

For the leaf peepers: Vermont

Photo titled Autumn in New England by GPA Photo Archive under CC BY-NC 2.0

Vermont is kind of the Mecca of New England fall. Roughly 80% of the state is covered in trees, which means the state is nearly blanketed in vibrant fall colors come October. The state is filled with charming tiny towns, quaint churches, and rustic farms, making it the perfect place to go when the leaves start to turn.

Everything I’ve read about Vermont suggests that it really is as pretty as it looks in the pictures, and maybe prettier. One of the best things to do in Vermont in the fall is to drive up Route 100. This 216-mile highway cuts through the length of Vermont, passing through the most epic scenery and cutest towns you ever did see.

I personally found planning a Vermont trip to see the leaves — or should I say “Leaf Peeping” — to be completely overwhelming. I think that’s because there were just so many little places to go, but not one great place to go. It also required a lot of driving, and I do not have a car.

If you’re looking for immediate help planning a Vermont road trip from New York City, check out this great guide.

  • How to get there from NYC: From New York City, drive north toward Wilmington, VT and go north on Route 100
  • Where to find fall: Cold Hollow Cider Mill, near Stowe along Route 100
  • What you’ll need: A car
  • When to go: Late September – Early October

For the train travelers: Montreal, Canada

Amtrak’s most scenic train route is finally returning in 2023! The route was halted for the pandemic in 2020 and didn’t resume again until spring 2023. You’ll definitely want to book this trip ASAP because this route sells out and can also get pretty expensive the closer you get to your travel date.

The 10-hour journey across 400 miles isn’t for the faint of heart, but the views are worth it. Throughout the day’s ride you will enjoy stunning views of the Hudson Valley and upstate New York as you make your way into Canada. As you would expect, fall is the quintessential time to make this epic journey. Plus, at the end you get to enjoy fall in Montreal which looks like a dream. We haven’t been to Montreal yet, but here is a great guide to the city in the fall.

  • How to get there from NYC: Take the Amtrak Adirondack train from Penn Station to Montreal, Quebec (10 hours)
  • Where to find fall: All around you. The left side of the train in the direction of travel will have the best views on the southern portion of the journey and the right side will have better views on the norther portion.
  • What you’ll need: A comfy flannel shirt and cup of crappy Amtrak coffee
  • When to go: Late September to Early October

For the haunting hunters: Salem, Massachusetts

Photo titled Witch Dungeon Museum by Mattia Panciroli under CC BY-NC-ND 2.0

There is no spookier Spooky Season spot than Salem, Massachusetts. The city is most widely known for the Salem Witch Trials in the late 1600s, and it’s also where the Halloween classic Hocus Pocus was set and filmed.

While many of Salem’s attractions are open year-round, the town is the most exciting in the weeks leading up to Halloween. Haunted Happenings take place the whole month of October and include special tours, haunted houses, a street festival and a parade. You can visit a variety of museums, pay your respects at the Salem Witch Trials Memorial and see the film locations from Hocus Pocus.

It’s pretty easy to get to Salem from New York City by train, but you do have to switch trains in different stations in Boston. If you ask me, this sounds like a great excuse to pair Salem with a couple days in Boston, too.

  • How to get there from NYC: Take the Amtrak Northeast Regional train from Penn Station to Boston South Station (4 hours). Walk 1 mile (or rideshare) from the South Station to the North Station. Then take the Newburyport/Rockport train (operated by Massachusetts Bay Transportation Authority) from the North Station to Salem (30 minutes).
  • Where to find fall: Salem Walking Tour (like this History & Hauntings of Salem tour)
  • What you’ll need: A recent Hocus Pocus screening
  • When to go: October

For the sweater weather seekers: Newport, Rhode Island

Photo titled RI – Newport – Bowen’s Wharf by Wally Gobetz under CC BY-NC-ND 2.0

I recently told my husband, in all seriousness, that all travel roads lead to Newport. I’ve romanticized this seaside town since I started following Kiel James Patrick on Instagram. (I do not care how much he Photoshops his pictures, he makes me watch to watch Harry Potter outside on a projector beside a 1:1 ratio of lit jack-o-lanterns to cozy throw blankets.)

Newport is about as idyllic in the fall as it seemingly is all year. It’s a picture-perfect seaside town that has long since been a haven for the wealthy, but its New England charm beacons to everyone who has ever popped their polo collar.

Highlights of a fall trip to Newport include the obligatory afternoon at Bowen’s Wharf, a stop at the Trinity Church Pumpkin Patch and a scenic stroll on the cliff walk.

  • How to get there from NYC: Take the Amtrak Northeast Regional train from Penn Station to Kingston. Then take the Rhode Island Public Transit Authority bus #64 from Kingston Railroad Station to Newport. (4.5 hours)
  • Where to find fall: Trinity Church Pumpkin Patch
  • What you’ll need: A new plaid flannel from from the KJP flagship store
  • When to go: October 13 – 31

For the autumnal academics: New Haven, Connecticut

Photo titled New Haven, Old Campus of Yale University by Klaus Wagensonner under CC BY-NC-ND 2.0

This one’s for the people who have strong feelings about pens and rewatch Gilmore Girls every autumn. If fall feels like back-to-school to you, you will surely find joy walking through New Haven in the fall.

Sling on your new backpack and walk down Chapel Street through the heart of Yale University campus. Visit the Peabody Museum of Natural History or the Beinecke Rare Book and Manuscript Library. Pick up a Yale crewneck and head over to the Yale Bowl to catch a football game if they’re in town.

Once you’ve explored the different quads and parks around campus, the real fall scenery is up at East Rock Park. Cozy up on a cute picnic blanket with a good book under an oak tree. It’s what Rory would have wanted.

  • How to get there from NYC: Take the Amtrak Acela train from Penn Station to New Haven. (1.5 hours)
  • Where to find fall: East Rock Park
  • What you’ll need: A worn copy of your favorite book (preferably something like Anna Karenina or the The Alchemist)
  • When to go: Saturdays in September and October, particularly when Yale has home football games (check the schedule here)

For the seasonal jet setters: London, England

If you’ve got the budget and time for an international trip this fall, consider a visit to jolly old England. London is one of my favorite cities and the fall is my favorite time to visit. The weather can be dreary, but that’s perfect for a city known for cozy pubs and indulgent comfort foods.

London has so many trees that according to the UN’s definition, it is technically a forest. So you can imagine the colors that blanket the city when fall hits. Whether you’re walking through St. James’s Park on your way to Buckingham Palace or riding the Uber Boat down the River Thames, fall foliage will follow you.

A trip to London in the fall is not complete without a visit to Borough Market. Indulge in seasonal favorites like pumpkin ravioli and hard apple cider. If there’s a break in the clouds, take a spin around the London Eye or head to the top of the Shard. End your day with a hot plate of fish and chips and a cask ale. It’s definitely the ultimate fall destination you didn’t know you were missing.

For the littlest leaves (aka kids under 3): Central Park, NYC

Is this cheating? I know this is not a trip from New York City, but it is a great way to experience fall without the stress of actual travel.

I’m sure I don’t have to tell a New Yorker this, but Central Park is filled with playgrounds of all sizes, rocks to climb on, and tons open space for kids to run and explore on their own. There are birds to watch, puppies to pet, and horse-drawn carriages clanking by. Parents can grab a bag of roasted cinnamon pecans from a food cart and enjoy a crunchy stroll through the fallen leaves.

The thing about small children is that they find joy in the simplest things. By the time they were two, our toddler had been to four countries, lived in three states and visited a dozen US cities, but do you know what their favorite part about all of these places was? Whatever playground they played on there.

My point is that travel at this stage is for the parents. If you like travel and want to bring your child on any of these adventures, do it! We would totally bring our kid to any destination on this list. But if the idea of getting your little one on a train or sleeping in a hotel stresses you out, don’t feel like you have to go somewhere extravagant to have an amazing fall experience.

  • How to get there from NYC: Take the subway
  • Where to find Fall: The Ramble (or Summerhouse at the Dene or Gapstow Bridge)
  • What you’ll need: A picnic lunch
  • When to go: October – November