A Fall Guide For The Adventurous New Yorker
The 5 Best Ways To Experience Fall Upstate |

Upon hearing the very first crunch of dried leaves on the sidewalk, talk of fall begins. Alistair Cooke, a celebrated journalist for the BBC, regarded the American fall with an almost religious reverence: “There are times of the year when anybody with an itch for travel must think of those parts of the earth that God favoured above all others when He handed out the seasons.” Indeed, fall is the time when the varied landscape of green hues gives way to a blazing canvas of reds, yellows, oranges, and browns; a time when pumpkins and apples are abundant and the chunky sweaters come out of storage.

With so many ways to experience this season’s charm, here are our picks for where to stay, eat, explore and shop, listed in order from closest to farthest from New York City.

Photo by Heidi’s Bridge

Best Fall Adventure Gear
Old Souls
Fall Guide to upstate, NY. andnorth.com

Old Souls
63 Main Street
Cold Spring, NY 10516

Fall is a prime season for outdoor adventuring and what every explorer needs – whether experienced or novice – is the right gear. Old Souls is your go-to destination for quality goods, be it field, stream, camp or home. The best part? They aim to feature local and American-made products whenever possible, supporting the sentiment that quality items should be handmade and built to last.

Photos by Emma Tuccillo

Best Seasonal Menu
The Village TeaRoom
Fall Guide to upstate, NY. andnorth.com

The Village TeaRoom
10 Plattekille Av
New Paltz, NY 12561

For owner and Executive Chef Agnes Devereux of the Village TeaRoom, sourcing local ingredients is an integral part of her commitment to seasonal cooking. Nearby farms supply the organic salad greens and vegetables that accompany the TeaRoom’s fall standouts, including a goat cheese sandwich with roasted vegetable spread, and a crisp roasted free range chicken with peach chutney, pan gravy, and scallion mashed potatoes.

Photos by Bri Stachowski

Best Fall Lookout
Route 44/55
Fall Guide to upstate, NY. andnorth.com

Route 44/55
1°44’41.4″N 74°16’14.5″W
This overlook is off of route 44/55. The view, from the Shawangunk Mountain Range looking out into the Catskill Mountains, is one of many places you can pull over, jump out, and take in the fall foliage. The overlook is approximately 25 minutes from New Paltz and 15 minutes from Kerhonkson (towns on either side of the mountain).

Photo by Bri Stachowski

Best Fall Orchard
Westwind Orchard
Fall Guide to upstate, NY. andnorth.com

Westwind Orchard
215 Lower Whitfield Road
Accord, NY 12404

Apple orchards are enough of a draw for any fall enthusiast, but add authentic Italian wood-fired pizza, and you’ve created every epicurean’s dream. In addition to selling apples, pumpkins, and gourds, Westwind also features a well-sourced local market with artisanal pottery, seasonal produce, and the orchard’s very own raw honey and raspberry jam.

Photos by Taylor Antisdel

Best Place To Stay For The Weekend
Spruceton Inn
Fall Guide to upstate, NY. andnorth.com

Spruceton Inn
2080 Spruceton Road
West Kill, NY 12492

Five miles down Spruceton Road is the Spruceton Inn, a picturesque respite that offers scenic views of the Catskill Mountains from every window of its nine rooms. Rise early with a hot cup of Cafe Grumpy drip coffee and embark on one of the many nature walks and hikes that lie just a few steps beyond your door.
Photos by Nana Hagel


  1. Love the fall foliage view! If I could find a place to live where there is warm weather all year round and could keep the fall foliage, I’d be in heaven!

  2. I love the high quality recommendations on your site. And the Alistair Cooke quote really rings true–I can’t wait to get to New York this upcoming fall.

    (Note: The images on this post are currently broken.)

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