The Perfect Upstate Fall Weekend Itinerary
Black Walnut Farm, a vacation rental in Saugerties, Hudson Valley, New York
So you booked your upstate vacation rental— congrats! Whether you’re staying here in Saugerties at Black Walnut Farm, or one of the other charming towns in the Hudson Valley (Kingston, Woodstock, Rhinebeck, Hudson, and their neighbors), you want to make sure you have the best possible game plan to maximize these stunning fall weekends.
We’ve put together an amazing itinerary, so bookmark this page of things to do in the area… because finding an ideal upstate vacation rental is only the first step of a memorable trip. Be sure to make some reservations, as things up here book up quickly in the height of the season!
Friday: settle in and relax— you’re upstate!
On Friday, drive up to the area (Black Walnut Farm, our rental property, is in Saugerties— only about 2 hours drive from NYC). You’ll want to start with picking up supplies for the weekend.
Our local Saugerties grocery store, Price Chopper, is huge and has all the basics. We also recommend a trip to Adams Fairacre Farms in Kingston for more specialty items, an amazing seafood counter, and all locally-farmed produce (12 minutes away from Black Walnut Farm). If you’re planning on grilling out, Smokehouse of the Catskills is THE place to buy fabulous meats, cold cuts, bacon and smoked meat, sausage, chicken, and steak. (Only open Thurs-Sat, 7 minutes away).
If you want to pick up some wine, check out Town & Country Wine & Spirits: they have a friendly, knowledgeable staff, great spirits selection (a lot of it local), and a decent international wine selection (4 minutes away). Windmill Wine & Spirits in town focuses on Natural Wine if you're into that sort of thing! (10 minutes away.)
Once you’re all stocked up, pop by The Dutch Alehouse (8 minutes away) for a pint and some delicious bites. This is our friendly neighborhood gastropub serving up craft brews & comfort food classics. Meats are locally sourced and smoked in-house, and the atmosphere is lively.
Saturday: Antiquing and Exploring
If you want to go into town first thing in the morning, grab breakfast at Love Bites Cafe (10 min away), a cute breakfast and brunch spot featuring farm-to-table ingredients and decorated with art from local artists.
Or simply grab a batch of bagels from Village Bagels (8 minutes away) in downtown Saugerties, and head back to chill in the Black Walnut Farm sunroom for a leisurely start to the day.
Next, head to the Saugerties Farmer’s Market (open Saturdays from 10-2, May 28-Oct 29). Are you even in the Hudson Valley if you don't go to the farmer's market? The answer is, no! It’s a lovely spot to pick up some farm-fresh produce, hear live music, and soak in the local scene.
Ready for some antiquing? The Hudson Valley is known as a true destination for everything from high-end antiques dealers to quirky thrift and vintage shops. Jim’s favorite place to go is in nearby Kingston: Milne Antiques is a real gem with highly curated items (20 minutes away).
While you’re in Kingston, stop by Kingston Consignments for a wonderland of eclectic vintage pieces. Back in Saugerties, visit Pop Vintage and the Saugerties Antique Center for one-of-a-kind finds.
For lunch in Kingston, stop by Black Eyed Suzie’s and grab picnic supplies to-go: their famous fried chicken is epic, but everything we’ve tasted there is delicious. We also adore Rosie General for their lovely deli selection, house-made pickles of every variety, fresh baked bread, sandwiches, salads and pastries.
Wrap up the afternoon back in Saugerties, browsing the vintage vinyl selection at Inquiring Minds Bookstore (8 minutes away). Treat yourself to a coffee there, or walk over to Olsen & Company for incredible espresso, artisan baked goods, and locally-made provisions like cheeses, jams, syrups, sauces, charcuterie, and honey.
Saturday evening, make a reservation at Miss Lucy’s Kitchen in Saugerties. This rustic farm-to-table cafe dishes up locally sourced American cuisine in a country farmhouse atmosphere. Great cocktails and you definitely want to save room for dessert here!
If you’re in the mood for something more casual, check out Main Street Restaurant for top-notch tacos, nachos, margaritas and yummy Southwestern fare (super family-friendly too). Finish off your night at local watering hole The Partition Bar. Tons of outdoor seating, cornhole games, live music and tasty bar snacks await (open through Oct 31st).
Sunday: Time for some nature!
One of the main reasons you probably booked an upstate vacation rental was to get more time in the great outdoors. The Hudson Valley and neighboring Catskills has an abundance of options for you!
For hiking, visit the Falling Waters Preserve (10 minutes away)— a nice, short (30 minute each way) hike through a nature preserve. Trails are well marked and maintained; suitable for regular shoes (hiking boots not necessary). Beautiful views of the Hudson, varied terrain, and waterfalls along the trail.
Opus 40 (10 minutes away) is considered by many to be 'the Stonehenge of North America'. A world-famous nonprofit sculpture park and museum with more than 60 acres of meadows, forested paths and bluestone quarries — including 6.5 acres of earthwork sculpture created over 37 years by pioneering artist and professor Harvey Fite.
Wear sneakers or hiking shoes, and don't miss the "museum" up the hill to see the tools Mr. Fite used to create this work! Yoga classes and life music evenings are offered there as well.
For family-friendly autumn fun, take the whole crew over to Rose Hill Farm in Red Hook (30 minutes away) for apple picking! You can also taste their cider and local wine in their taproom, or enjoy local food trucks all season long. Check out their events— you might catch a yoga class in the orchard or some live music.
Or, visit the pumpkin patch at Kelder’s Farm in Kerhonksen (35 minutes away). While you’re there, take a hayride, explore their corn maze, visit with farm animals, enjoy local treats like kettle corn and cider donuts. They have a pizza barn as well as craft beer and wine. You could easily spend the whole day here in a whirlwind of fall fantasy.
Wrap up your weekend with an alfresco cocktail at Cooper’s Daughter Spirits at Olde Yorke Farm in Claverack (40 minutes away). Visit this charming distillery, offering spirits tastings and a creative cocktail menu in the lovely outdoor garden— with food trucks every weekend! Make sure you buy a bottle of their Black Walnut Bourbon to bring home with you (it’s our house pour for sure).
No matter if you’re into farm-to-table dining, outdoor adventures, or antiquing and exploring, the Hudson Valley has something for everyone. We hope you enjoy your stay— and if you’d like to stay at The Black Walnut Farm and haven’t booked yet, fill out our inquiry form for your reservation. We can’t wait to welcome you!