Autumn Leaf-Peeping in Woodstock, NY

Long before the Hudson River hamlet lent its name to the hippie hordes, the Woodstock area was known for its beautiful fall colors and vibrant art scene.

By Maria De La O

Woodstock and its adjacent towns have long been a draw for artists and nature-lovers of every stripe. Beginning with the Hudson River School painters and Arts & Crafts movement of the late 1800s, through the late ’60s when Jimi Hendrix and Bob Dylan stayed here, to the present day, this corner of the Catskills has long beckoned edgy New Yorkers into the woods.

Here you’ll find upscale boutiques and farm-to-table cuisine, wealthy artists, a Buddhist monastery, yoga and New Age provisions, a world-class film festival and a “music chapel” in the woods, as well as a healthy dose of shops trading on the hippie past in Woodstock’s town center.


The ROAM Report – Woodstock, New York

Travelers: Alice, Maria and Vivi (4)

Date: 3 days in October 2017

Itinerary: Woodstock, New York

Budget: About $1,500 for airfare for three from the West Coast and less than $500 for accommodations.


The Good Stuff

Hangry No More – The Hudson Valley is a foodie paradise with farm-to-table cuisine ruling the scene, and after checking out the options in Woodstock, we decided the place to be for brunch was Oriole 9. From the kids’ menu to the prosciutto-and-cheese plate to the poached artichoke filled with scrambled eggs to the Cuban press coffee, we all left satisfied and fueled up for the rest of the day.

Take a Walk  The best way to see the local flora and fauna is to get those kids out on the hiking trail, and since Woodstock is situated within Catskill Park, where nearly half the land is protected by the state or by New York City, there are plenty of trails to choose from. Some of the more popular hikes are the trails to Overlook Mountain (uphill, but there are some cool ruins of an abandoned hotel at the top), Cooper Lake (the largest natural lake in the Catskill Mountains, located almost directly behind the village of Woodstock) and the three-mile paved paths (perfect for strollers) along the Ashokan Reservoir, which provides the drinking water for New York City.

We chose the Poets’ Walk, a relatively flat route that features the Overlook Pavilion (pictured), outside Rhinebeck for its purely romantic-sounding connotations. Afterward, we headed into Rhinebeck proper to quaff our thirst and fill our bellies at the Liberty Public House, a Gothic Revival library-cum-restaurant now charmingly cluttered with antiques.


Chasing Waterfalls  Right in the middle of Woodstock, along Tannery Brook, is the little Woodstock Waterfall Park, a pocket park that attracts the stroller set and overlooks a pretty spectacular waterfall. You can also walk down from the park to check out the waterfall and stream up close.

Kaleidoscope Eyes  About 20 minutes outside of the village of Woodstock is Mount Tremper, where you can find the Guinness book­–certified largest kaleidoscope in the world, which is on the grounds of the Emerson Resort. Made from a converted grain silo, the kaleidoscope is measured at 56 feet tall, and you can watch the video and sound show in the ’scope by lying or sitting on the floor and gazing skyward. Groovy!

Peace, Love and Cupcakes  Perfect for an afternoon sugar break, this cupcake shop does not disappoint. Opened by a former jingle singer who went on win the 2008 Food Network competition for “best cake in the country,” this place on Woodstock’s Tinker Street is only open on weekends and has a rotating menu of cupcakes like The Signature Tie-Dye and the Jimi Hendrix (triple-shot espresso cake with mocha buttercream). 

Bang a Drum  If your kid is anything like mine, a good old-fashioned hippie drum circle is irresistible. Whether its drumming, dancing or just watching, take a break from all the Woodstock village shops by heading down to the Village Green on Sundays from about 4 p.m. to 6 p.m. When the weather gets too cold for drumming outside, word is you can find the drummers inside the nearby community center.

Walkable Art  Closer to the Woodstock-adjacent town of Saugerties, you’ll find Opus 40, a 6.5 acre bluestone sculpture that you and your kids can walk through, over and under via subterranean pathways that creep 16 feet below the ground. The sculpture grounds are located in the shadow of Overlook Mountain and various hiking trails spin off from the site. A perfect place for a picnic, the arts center here also sponsors various concerts and events, so check the schedule before you visit.

The Not So Good

Timing Is Everything  Longtime residents may tell you that leaf-peeping season is best during the second week of October, but we were definitely on the early side at that time and the weather seemed unseasonably warm and wet. Further research indicates that, perhaps due to climate change, the best time to catch the fall colors in the Catskills may be a bit later in the season, close to Halloween. Your best bet is to look at prediction models over the summer to get your reservations in advance of the throngs, and then pray you guessed right. If you try to wait until the last minute, there won’t be any room at the inn.

Good to Know

This is bed-and-breakfast country, but can you really see your kid staying at a Colonial-era home filled with fragile antiques? Even if the establishment allows kids, which is unlikely, it would be a heart attack waiting to happen. So do your cardiologist a favor and check Airbnb or VRBO for deals on cottages, which tend to be quite affordable.


 Maria De La O – October 2018

ROAM Executive Editor   

Magazine editor. Documentary filmmaker. Copy expert. Mother. Traveler. Maria brings it all to the pages of ROAM.  maria@roamfamilytravel.com

© ROAM Family Travel 2019 – All rights reserved


ROAM with us! Read more REAL family adventures


Don’t miss a single trip! Enter your email address in the box below to subscribe to ROAM and receive notifications of new posts by email. Check your inbox for an email to confirm your subscription, click the link and you’re ready to ROAM!