Colorful fall foliage, mountain roads, “All Too Well” on the car stereo, freshly-picked apples in the backseat… it's the most wonderful time of the year if you're obsessed with Gilmore Girls or Christian girl autumn or Halloween. My family and I recently made the most of it — we set out to craft the perfect fall trip, and we pretty much succeeded. The keys: imagination, a go-with-the-flow attitude to changes in plan, and a great playlist.
Below, here's what we learned about planning a fall foliage weekend getaway, complete with jack-o-lanterns, apple-picking, scary movies, and more.
Start with a vibe
Vacations — even small ones! — are a chance to create a fantasy version of ourselves (and the people we’re traveling with), so let your imagination run free. Half the fun of getting away is planning how you’ll do it, and studies have shown the anticipation of something fun can be even greater for you than the actual event.
The mood, the abstract energy, the filter that will overlay your memories — the vibe shapes everything that comes next, including where to stay, how to get there, and what you’ll do when you arrive.
My sister Marianne, our mom, and I knew we wanted a Gilmore Girls, folklore/evermore, Pretty Little Liars-hued type of fall foliage trip; the kind where you wear classic UGGs and wrap up in a cozy blanket and watch lightly scary movies in a cabin in the woods as leaves gently float down outside the window. We started with that and built out from there, eventually landing on the Catskill Mountains in upstate New York, about three hours from New York City.
Find a place to stay that’s close, cute, or cost-conscious (ideally, a combination of the three) and plan your route
The Catskills aren’t easily accessible by train, so we rented a five-seater Volvo XC60 midsize SUV (provided at no cost for this article by Volvo) and headed up early Saturday morning. Knowing we had a car opened up our choices for lodging — and the large Google Maps screen made sure we never got too lost. We planned to explore a variety of towns across the mountains and even down closer to the Hudson Valley, but we also wanted a place to stay that was more affordable; we were looking to spend $50-100 per night each. We didn’t need to be in the more popular towns, like Kingston, Windham, or Tarrytown, all of which are beautiful but also a bit pricier (and more crowded).
Those decisions led us to a tranquil Airbnb in Denver, NY, nestled in the Catskills. (Airbnb provided a credit for about 70% of our stay for this story.) The A-frame three-bedroom house we stayed in was spacious and had everything we needed for our five-day stay, including a fire pit, an L-shaped couch large enough for the three of us to lounge comfortably, and a back porch with a gorgeous forest overlook. We had neighbors down the road, so it wasn’t totally isolated, but it was quiet and peaceful without a lot of road traffic. The total cost for four nights was $1400, not including the credit — so it would’ve come out to $466 per person, over our budget but worth it for us to each have our own bedroom.
You could find similar rates (or even less expensive) in the Catskills depending on your flexibility with location and size. If you’re looking for a dreamy fall getaway in another location, you could also expand your search to areas in Connecticut and Massachusetts; Airbnb reports that North Dakota, Maine, and Massachusetts had the highest percentage of stays in the fall. And for the record, you can also broaden your horizons beyond the tri-state and New England — there's plenty of beautiful fall views across the U.S.
Make a collaborative playlist
Every roadtrip needs a roadtrip playlist, and for ours, I created a collaborative Spotify playlist a week or two prior and shared it with my mom and sister, who each added songs they liked. Marianne and I went for more of a clear autumnal vibe, while our mom chose hits from the ‘70s and ‘80s — leading to some iconic transitions, such as Mitski’s “My Love Is Mine all Mine” into “Funkytown.”
The speakers in the Volvo were noticeably higher quality than I’m used to in Ubers around New York City, with a sound system custom-created by Bowers & Wilkins (who also make my favorite pair of headphones). We also kept an “All Too Well (10 Minute Version)” counter, landing at seven plays all the way through before we simply could not listen to Taylor Swift’s fall magnum opus again — and began to seriously question why a playlist with over a hundred songs kept bringing us back to the same one.
Choose one or two splashy fall activities
Don’t overpack the schedule! My sister did the bulk of our trip research, bringing us a mapped out itinerary of ideas for low-stakes fall activities; she didn’t have us doing too much on any one day and left room for any unpredictable changes in plan, like weather or holiday weekend closures.
We focused our trip around two main goals: apple-picking and visiting the Great Jack O’Lantern Blaze near Sleepy Hollow. We bought a ticket for the Blaze for Wednesday night ($47 per person) at the end of our trip, and then planned to do the former at Stone Ridge Orchard on Monday, hoping for fewer crowds. Stone Ridge was closed for Indigenous Peoples Day, however, so we pivoted to Tuesday — and arrived to find it basically empty, getting the large farm to ourselves. The weather was beautiful, sunny and not too cold, and we plucked Macintosh, Gala, and Asian pears ($8 for a small bag), munching on a couple as we walked through the orchard. At the farm stand, we picked up blueberry and apple pies, and cider for later.
The perfect spooky season activity was the Great Jack O’Lantern Blaze, which has two locations in Tarrytown and on Long Island. It’s a huge walk-through art exhibition of increasingly detailed carved pumpkins, with extravagant light shows and references to classical art, history, and the legend of Sleepy Hollow. It takes about 45 minutes to an hour to make your way through the maze-like trail, and there’s parking on-site. (It’s also walkable to the Croton-Harmon stop on the Hudson line of Metro North.) It’ll definitely leave you inspired to do a little pumpkin carving of your own — or maybe to just leave it to the pros.
Embrace side quests
With a big activity or two set in stone, you leave space for those deviations off the path, the side quests and little adventures that create the fond memories that make a vacation most meaningful.
We ended up taking a picturesque nature walk through the just-turning leaves in New Paltz, exploring a local fall festival and eating funnel cake near a church that looked straight out of Pretty Little Liars in Windham, and looking into the world’s largest kaleidoscope following apple cider pancakes at Phoenicia Diner.
Later, we wandered around Rhinebeck, New York, stopping in at Samuel's Sweet Shop (co-owned by One Tree Hill's Hilarie Burton!) for a t-shirt and coffee and popping into the town's many other shops and eateries.
Enjoy the moment—but take a photo or two
No one likes taking a vacation with people who are on their phone 24/7, but it's the human condition to want a few great photos for social media. The selfie below was taken (on the iPhone 16 Pro Max) on the road after apple-picking. But the real memories come not from photos, but from the time the three of us spent together: all our new inside jokes, our amateur food reviews, the songs sung in the car on the drive back to New York. Fall as a backdrop for one of the best weekends with the people I love most.
