Colorful New York: A fall foliage road trip

Last Updated on August 20, 2024

I am not sure when I started to dislike fall, but I think it must have been during my years in England. Fall, or autumn as the Brits say, always seemed to define itself through rain and foggy days, and while those misty London mornings could be romanticized initially, the novelty wore off quickly, replaced by the melancholy over yet another rainy day.After I’d packed up my London apartment and started traveling the world indefinitely, I started chasing the sun and I skipped spring, winter and autumn completely. Until I happened to find myself in the U.S. in October one year, amazed by how colorful and sunny this season was in the Midwest. It was my first time experiencing pumpkin patches, corn mazes and pumpkin spiced treats. Suddenly, autumn felt wonderful, and not dreary at all. Instead of rainy days and grey skies, I was enchanted by blue skies and autumn leaves in vibrant colors.When I was told that those colors weren’t even the most colorful ones in the U.S., but that the trees on the East Coast, New England in particular, had even more vivid fall colors in October, I put a New England fall colors road trip on my travel wish list right away.I was hoping to finally fulfill this dream last year, but  when I came back to New York for a few weeks in October, I ran out of time and ended up going only on a day trip to the scenic Seven Lakes region in Upstate New York.

A New York fall foliage road trip

So this year I was determined to finally head up to Vermont. Spoiler alert: I still didn’t make it there! However, I managed to go on an epic New York fall foliage road trip for several days, instead of just a rushed one day out-of-town getaway. And yes, I could’ve made it all the way up to New Hampshire and Vermont, but I wanted to set some time aside to enjoy the scenery, go on hikes and unleash my inner child in the leaves (which I did), picking up farm-fresh apples and stopping in random little towns along the way, instead of spending all too much time in the car.
Shortly after crossing the George Washington Bridge and leaving Manhattan, we found ourselves surrounded by vibrant fall colors along the Palisades Parkway, which would bring us to our first destination: Bear Mountain State Park, about 50 miles north of New York City.

We wanted to attempt climbing up to the peak of the mountain, from where I knew we’d have fantastic views over the Hudson River and when the weather was good you could see four states from the top of Perkins Memorial Tower atop of the mountain: New York, New Jersey, Connecticut and Pennsylvania.The hike, which took about three hours in total, was steep at times, but the panoramic vistas were definitely worth the climb.My plan was to stay in cozy cottages or B&Bs throughout the trip, which is why I spent hours researching places on AirBnB. Accommodation can make or break your New York fall road trip – I am recommending some of my favorite finds at the end of this post.We crossed the river and continued on east of the Hudson River because we wanted to stop in Poughkeepsie the next day, where we wanted to cross the Hudson once again – but this time, on foot. The Walkway Over The Hudson, which is at 1.28 miles the longest pedestrian bridge in the world, seemed like the perfect place to take in the fall foliage from. At 212 feet above the river’s surface, it isn’t for the faint at heart but I kept my fear of heights under control by staying away from the rails.I loved how beautiful the yellow leaves on the trees on the path leading up to the bridge looked, forming a natural ‘tree tunnel’. The walk over the bridge and back takes about an hour, depending how often you stop to take pictures.After that, we headed further north into the Catskill Mountains west of the Hudson River. For the drive I chose route 32, which passed through the towns of New Paltz, Kingston and Woodstock – and it ended up being unbelievably scenic at this time of year. We couldn’t help but stop in several of the towns to check out some antiques shops and galleries along the main roads. Seeing these charming towns all dressed up for autumn, with pumpkins decorating entrances of houses and window sills, stacks of hay, fall flowers and restaurant menus denouncing seasonal specials, filled me with so much joy.

We stopped on the side of the road to pick up some farm-fresh apples, but we could’ve easily filled the car with just about everything the farmers were offering: homemade jams, pumpkins in all shapes and sizes, apple cider and fresh honey.The next morning, I woke up just in time to witness a spectacular fiery red autumn sunrise, the air wonderfully crisp, the kind of day that is perfect for a hike through the woods and is waiting to be finished with a mug of hot apple cider by the fireplace. We had made our way all the way into the Catskills Mountains, but the further north we went, the barer the trees had become – here, the leaves had already fallen from the branches, leaving the ground covered in brown and red leaves.That wasn’t a bad thing though – on our hike to the Kaaterskill Waterfalls the leaves felt like a soft carpet on the ground, causing a crackling sound in the otherwise silent forest as our feet touched them. I could have spent many more days hiking in the Catskills – a list of trails I had found online made me wish I had time for some of the longer hikes in these mountains.But luckily the Catskills are en route to Vermont’s scenic Green Mountain Byway, which I hope I’ll finally make it to next year.

Practical information for your own New York Fall Foliage Road Trip

• The State Of New York publishes a fall foliage report for all regions, which helps you to find out the perfect time to go.
• Towns along the way worth stopping in: Rhinebeck, Catskill, Tannersville, Woodstock and New Paltz.
• Book your accommodation early, especially if you’re planning a fall colors weekend getaway: the cutest Airbnb’s book up months in advance.

Places to stay near Bear Mountain:  

Check out this cozy place in Warwick (about half an hour from Bear Mountain), this 3-bedroom cottage in Cold Spring (about 15 minutes away) and this affordable studio apartment in Beacon (about 30 minutes away).

Places to stay in Woodstock:  

• Morning Glory B&B – Charming B&B with a lovely garden
• Hotel Dylan – Small hotel right by the Ashokan Reservoir
• Woodstock Way Hotel – this fabulous hotel is a splurge in a great location in the center of Woodstock

If you’re a larger group, check out the quirky Woodstock Barn House, which has a sauna, gym and jacuzzi, and sleeps 10 people.

Places to stay in Catskill:

There are plenty of rentals here because Catskill is lovely – check out this cabin 10 minutes walking from the center of Catskill, this stunning villa that was featured in House Beautiful Magazine and sleeps 8 people, and this this small downtown studio apartment.

Other places to stay in the Catskills area:

Resort & Spa

• YO1 Health Resort near Kiamesha Lake (resort with a state-of-the-art wellness center, indoor & outdoor pool, yoga, Ayurveda, etc…)

Bed & Breakfasts

• Tin Brook Bed &Breakfast – affordable guesthouse in Walden
• Mountain Treasure Bed & Breakfast – Lovely, affordable guesthouse in Windham
• Black Creek Bed & Breakfast – stunning guesthouse with a shared lounge, sun terrace and garden in Highland
• The Roxbury – Guesthouse with unique, individually themed rooms and a spa, hot tubs, dry sauna, steam rooms, as well as complimentary breakfast in Roxbury

Budget Hotels

• Courtyard by Marriott in Poughkeepsie – nice budget hotel with spacious rooms and an indoor pool
• Hampton Inn by Hilton – very good budget hotel in New Paltz
• Hampton Inn, Kingston
• Holiday Inn Express in Lake Katrine (near Kingston)

Have you done a New York fall foliage road trip? I’d love to hear all about it in the comments below!

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