The Seasonal Stuff

For every season there is a reason to come to Dutchess County! From antique car shows to pre-broadway summer theater; from county fairs to pick-your-own Christmas trees; there is always a reason to spend a weekend in Millbrook, NY. Below are just a few; reach out to us for dozens more!

The Millbrook Horse Trials

Held every summer, this is one of the largest equestrian competitions on the East Coast: where top riders from around the world use the event as an opportunity to get their horses ready to qualify for the international and team competitions that dominate the Fall season.
What's also great about this event: its free to the public! Spectators are given free entrance into the 4 day event, and are allowed to roam around the grounds and watch hundreds of horses and their riders in the dressage, jumping, and cross country events that take place throughout the day. Attendees will also get a chance to enjoy the wide array of local restaurants and vineyards who set up booths for annual event. 


Powerhouse Theater Festival

A summer staple for 35 years, this summer theater season is a partnership with Vassar College and New York Stage and Film. Its an opportunity to see complete shows before they make their way to broadway, but also works-in-progress: Hamilton famously was workshopped here. You can purchase single tickets, or for the season. But this is something you need to plan ahead, as tickets sell out fast. Check their schedule and order tickets online. As its less than 30 minutes away from the inn, we make a great place to stay for your all your summer theater needs. 

Box office: 845-437-5599 (open Jun-July)

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Dutchess County Fair

August means there's is a county fair happening somewhere...and the Dutchess County Fair is not only recognized as the largest agricultural fair in NYS, but
industry "insiders" know this is the best 6-day fair in the country. Formed in 1841, it is also one of the oldest! It has grown from a purely agricultural fair to one that also features nightly live concerts; amusement park rides and foods; animal races, turn-of-century life with live blacksmith demonstrations, dog competitions, and a horticultural center with dozens of themed gardens. Located in Rhinebeck, it is only a short drive north of the inn, which makes us a great base to really experience all the fair has to offer. There is a fair app to download to purchase tickets and follow each day's sked, so you don't miss a thing.

Tel: 845-876-4000

Spring Antiques At Rhinebeck

Held every Memorial Day weekend, this iconic antiques show spans two days and features dozens of exhibitors from all over the country. It features rugs, jewelry, furniture, porcelain and ceramics, books, folk art, textiles, watches..there is really something for everyone.
Let the inn give you an early breakfast, so you can get an early start and be ready to shop till you drop!


Pick-Your-Own Farms

The area is surrounded by all sorts of "pick-your-own" farms for every season: from pumpkins and apples in the fall; Christmas trees in December; or berries in the spring; there is always something to pick. It's a great way to connect with the land, and to keep enjoying it for days after you are back home. Try Fishkill Farms, beginning with strawberries in June and ending with pumpkins and a cider bar in October (and everything else in between). Barton Orchards is the premiere apple orchard in the area, with a farm-stand and shop that sells their own cider (and cider donuts of course!). Evergreen Farm is your full-service Christmas wreath and tree farm: they will cut and carry it to your car for you, or they will lend you the tools to do it all yourself.

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The Millbrook Inn, 3 Gifford Road, Millbrook, NY 12545