10 Fall Days in the Hudson Valley

This weekend I couldn’t help but notice that the leaves are slowly starting to change, that some mornings when I wake up there’s a crispness to the air that feels a bit like fall, and that summer is starting to slowly drift away.

Last year I very intentionally planned a bit of time off around peak leaf season and thought now seemed like a good time to share my itinerary for 10 fall days in the Hudson Valley.

Day 1: Dutch’s Spirits, Pine Plains

Dutch’s Spirits in Pine Plains is not only a great spot for a drink, but also offers some very picturesque views of the mountains and their changing leaves. They’re dog-friendly and while it seems like they might just be offering a tasting menu these days, be sure to check out their Instagram for the latest because we’ve had the best cheeseburgers and BBQ there in the past. Dutch’s is near Stissing Mountain – great for a hike and is a short drive to Millerton, which is “enjoying a renaissance” according to Hudson Valley Magazine (be sure to stop at Hammertown on the way for some design Inso too!).

Day 2: Mills Mansion, Staatsburg

Mills Mansion is in my opinion the most under rated historic home in the Hudson Valley, which I love – because it means there’s very rarely a crowd. Pack a picnic lunch (we like to grab sandwiches from Adam’s) and take one of the most scenic fall walks around. If you head down toward the water and take the trail into the woods, you’ll see more than one historic mansion while you’re here! Mills is also very close to Rhinebeck, which means you can stop at Paul Rudd’s candy store, or grab a wood-fried pizza from Posto’s (fun fact: a Hallmark movie shot here!).

Day 3: Ashokan Rail Trail

The Ashokan Rail Trail is best enjoyed an hour or so before golden hour (at the Woodstock Dike Trailhead) – the trail goes on for miles, but you don’t need to walk far to see water and land and leaves. The trail is near enough to Woodstock, or Kingston to check out either town during the day. If you’re in Kingston, be sure to check out Sissy’s for a great sandwich (breakfast or otherwise), Rough Draft for a drink, and Kingston Bread + Bar for something sweet. We also love Santa Fe for a taco and margarita date night.

Day 4: Saugerties Lighthouse, Saugerties

Percy and I just love the Saugerties Lighthouse, if you follow me on Instagram you probably know we go there A LOT. The walk is beautiful in every season and the lighthouse is my dream house, it’s brick and charming and in the middle of what feels like no where.

Day 5 and 6: Mohonk Preserve, New Paltz

The Mohonk Preserve has a lot to offer (like multiple days worth) – we like to park on Pine Road and take the Gatehouse trail, but we also like spots like Minnewaska State Park.

Darren and I love driving to New Paltz on weekends (a little under an hour from us) and grabbing lunch from Schatzi’s (get the Pretzels and Pierogies to start and the Bier Cheese Soup and Glenn’s Reuben as a main and thank me later!) or Twin Star Orchards – both dog friendly! New Paltz is also the perfect town to walk about, there are some great shops on Main Street, including a jewelry store, a vintage spot, and more.

If you’re heading back North, Ollie’s Pizza is another great dog-friendly spot with lots of outdoor seating.

Day 7: Vanderbilt Mansion, Hyde Park

The best way to experience Vanderbilt is to drive through Rhinebeck on the way and pick up Rhinebeck Bagels breakfast sandwiches (Darren’s order is the GWB and mine is the Busta B). There’s just something about eating a breakfast sandwich on the steps of a 54-room mansion that makes it even better.

Day 8: Clermont State Historic Site, Clermont

I like to think of the Clermont State Historic Site as my little secret, while one of the smaller mansions of the Hudson Valley, this one is really beautiful, maybe even provincial and the property offers a lot – the main house, a cottage, a barn, and ruins. There are also Hudson River views and lots of spots to take it all in. The site is also very near Lasting Joy, a dog-friendly brewery Darren and I just checked out and really liked (try their Belgian Wheat and check their Instagram for the latest on food pop-ups).

Day 9: Olana and Warren Street, Hudson

If you’re looking for a truly special lunch, grab lunch from Talbott & Arding (I like their soups and sandwiches and cakes and puddings) and sit in the same spot as Hudson River School painters while you enjoy a vast view of the valley. Warning: this one gets crowded on weekends! After lunch on the hill, take in Warren Street in Hudson, where you’ll find coffee, antiques, and impressive architecture.

Day 10: Cooper’s Daughter Spirits, Claverack

Cooper’s Daughter Spirits is a barn turned cocktail garden with inventive drinks and so much warmth – while you won’t spot sprawling Hudson Valley views here, this spot is perfect for an afternoon of good company and great drinks (also dog friendly!).


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