Your Guide to Hudson Valley Fall Activities

As one of the top 5 Inns to visit in the fall, Caldwell House sparkles as the leaves begin to turn. Both the building and the grounds glow as if they were made for fall! The surrounding countryside is full of iconic fall activities; the problem is, which one to choose? To help you discover the range of fun, here is your guide to Hudson Valley fall activities in our little corner of heaven. 

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 18  |  10am – 5pm
Main St, Cornwall NY
This year will be the 50th Fall Festival in Cornwall! Main Street will be lined with vendors, both food and craft, and there will be numerous live musical acts.

The Big Sip: A Wine & Spirits Festival
October 8 & 9  |  1pm – 5pm
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!

Hudson Valley Farm and Flea Market
October 8  |  10am – 4pm
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!



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! Here is a list of local farms with apples for picking (or buying) and corn mazes.

If you really want to get into the Halloween spirit, get your tickets now for the Great Jack O’Lantern Blaze. What is that? A display of over 7,000 illuminated Jack O’Lanterns with synchronized lighting and soundtrack. Rip Van Winkle would lose his head over it!

Doesn’t this make you want to pull out your flannel shirt and pumpkin spice-flavored beverage? We are sure that this 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.


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