Your Guide to Hudson Valley Fall Activities

Updated August 2023

As one of the top 5 Inns to visit in the fall, Caldwell House sparkles as the leaves begin to turn. To ensure you don’t miss a single sight, we have put together your guide to Hudson Valley fall activities for our little corner of heaven. 

Both the building and the grounds glow as if they were made for fall! If you are one that scrolls social media, your feed is probably full of everything pumpkin spice, fall decor, and comfort food recipes. It’s an amazing time to travel and the Hudson Valley in upstate New York is absolutely one of the best places to be in fall. 

Book your stay early, it is a popular time of year! Can’t you just smell the mulled apple cider and hear the crunch of the leaves under your feet? 


Everyone loves a fall festival! With the crisp cool air, the smell of pumpkin spice, and a light jacket, you can taste, sip, and shop your way through the stalls. Here are our favorites:

Cornwall Fall Festival
September 21  | 10 am – 5 pm
Main St, Cornwall, NY
This year will be the 51st Fall Festival in Cornwall! Main Street will be lined with vendors, both food and craft, and there will be numerous live musical acts.

Grape Stomping Festival at Robibero Winery
September 23 – 24 & September 30 & October 1 | 11 am – 5:30 pm
714 Albany Post Rd, New Paltz, NY

Who doesn’t love purple feet? You can also enjoy lawn games, wood-fired pizza, and caramel apple sangria. There is live music, of course.

Garrison Craft Fair
September 30 & October 1 | 10 am – 5 pm
23 Garrison’s Landing, Garrison NY
Come see talented artisans displaying their work in a gorgeous setting overlooking the Hudson River. Items include furniture, jewelry, fiber art, ceramics, decorative art, and more

The Big Sip: A Wine & Spirits Festival
October 7 & 8  |  1 pm – 5:30 pm
200 Hurd Rd, Bethel, NY
Enjoy wines from the Finger Lakes, Hudson Valley, Long Island, and beyond! There will also be a great selection of spirits. In addition, enjoy live music, local crafts, and, of course, great food! This year enjoy Andrew McMahon in the Wilderness on Saturday and Back to the Eighties Show with Jessie’s Girl.

Hudson Valley Farm and Flea Market
October 7  |  10 am – 4 pm
Museum Village, 1010 Rt NY 17M, Monroe NY
Get a chance to see a curated collection of Hudson Valley’s most talented artisans and innovators in one place. There will be farmers and chefs with local produce and baked goods. 


Sometimes it is just easier to sit back and let someone else plan your day for you! All you have to do is show up. Here are our favorite fall tours:

Fall Foliage Wine Tour
Hudson Valley Bucket List  |  845-943-9490
This tour covers a lot of ground with foliage, visits to three unique wineries, and a catered pop-up picnic lunch! Plan to spend the entire day, and bring your camera.

Hudson River Cruises

Pride of the Hudson
Pride’s Landing, Newburgh NY  |  845-220-2120
What better way to enjoy fall foliage than on the water? Start in Newburgh, NY and go past Washington’s Headquarters, Breakneck Mountain (quarries at the bottom actually provided material for the base of the Brooklyn Bridge and the Statue of Liberty), and West Point.

Hudson River Sightseeing Cruise
40 Roundout Landing, Kingston NY  |  845-340-4700
This tour goes along the Hudson River in the opposite direction, and you will see several famous mansions (think Vanderbilt), as well as the Rondout and Esopus Lighthouses, all while gazing at the gorgeous fall scenery of the Hudson Valley.


Maybe you want to get in the car and take a drive to view the vibrant fall foliage. When is the best time to visit the Hudson Valley to view the most fall color? Of course, it can vary every year, depending on the amount of rain, and the temperatures, but the best show is usually in mid-September. You can check the progress of the changing of the leaves on the handy NY foliage report!

Several of the best routes and sights in the area include:

  • The Old Storm King Hwy (Rte 218, Cornwall) stretches from Cornwall to West Point, with many views of the Hudson River as it circles Storm King Mountain.
  • Shawangunk Mountains Scenic Byway (Rte 52, Pine Bush) will give you a breathtaking view of rural New York as the Dutch would have initially seen it. You will have access to more than 30,000 acres of natural preserves should you decide to exit your vehicle.
  • Seven Lakes Drive (Tiorati Circle on Rte 6, Bear Mountain) If the Appalachian Trail is on your bucket list, this drive takes you through Harriman State Park to Bear Mountain. If you want to exit your vehicle, you can hike part of the trail!
  • The world’s longest pedestrian bridge is located not far from our inn—the Walkway Over the Hudson. At 212 feet high and 1.28 miles long, it’s a nice place to find sweeping views of the valley and the Hudson River.
  • The Mohonk Preserve is a 7,500-acre section of land on the Shawangunk Ridge. You should check out Sky Top, a popular 1-mile path that leads up to an enormous stone tower where some say you can see six states on a clear day.
  • The Storm King Art Center, just minutes from our inn, is the country’s largest sculpture park, and the fall season creates a beautiful backdrop for the works of art.
  • The United States Military Academy West Point offers tours from the Visitor Center that take you to high points on the property where you can see breathtaking views of the Hudson River.
  • Take the Scenic Byway from Elks-Brox Park with a right onto Route 97. You’ll get to Hawk’s Nest, a twisty stretch of road that hugs the mountain. It is a fun route to drive that has been featured in several car commercials!


There are many other fall activities that are iconic for fall in the Northeast, like apple picking, corn mazes, and pumpkin carving. A lot of these activities can be found at the same place! 

Apple Picking: For apple lovers out there, there is some fantastic apple picking in the Hudson Valley! It’s so fun to head out to a local orchard and pick them fresh off the tree! During your stay with us, you can follow the Warwick Valley Apple Trail. It will take you to six different orchards and is a great way to see the beautiful scenery of the area and enjoy the bounty that the local farmers have to offer. 

Corn Mazes: Get lost in a corn maze – Whether you are traveling with young ones or not, enjoy some old-fashioned fall fun by going through a local corn maze! There are several farms and orchards near our bed and breakfast offering corn mazes, pumpkins, farm stands, bakeries, and more. Check out one of these below:

Enjoy the Great Jack O’Lantern Blaze: Held at Van Cortland Manor, a historic home in Croton-on-Hudson, the Great Jack O’Lantern Blaze is the coolest Halloween event with more than 7,000 intricately carved, glowing pumpkins. This one-of-a-kind event will take place from September 15 – November 19, and you have to purchase tickets in advance. It’s an event you don’t want to miss!


Doesn’t this make you want to pull out your flannel shirt and pumpkin spice-flavored beverage? We are sure that your guide to fall activities in the Hudson Valley will help you pick your dates and start to plan the perfect getaway at Caldwell House Bed and Breakfast. Need help with planning? No worries, we can easily give you restaurant recommendations, arrange a special massage, or, if you are visiting in September, arrange for our popular pie on the pillow!


Leave a Reply

Your email address will not be published. Required fields are marked *