Moving Guide

8 Don’t-Miss Annual Events Near the Hudson River

Festival season in the Hudson Valley kicks into high gear as soon as the summer rolls around, then continues through the end of the year. Every town along the Hudson River also has its own annual celebrations, often honoring whatever crop happens to be harvested at the moment, so do a little research before your visit.

It’s no surprise that all of the events listed below take place outdoors. Locals love the chance to explore the region when its springtime yellows turn to summer’s velvety greens.

The Hudson Valley’s Best Events in Summer

Summertime festivities draw huge crowds, so make sure to plan ahead. Whenever possible, make sure you purchase tickets ahead of time, especially if you have your heart set on a special event.

Hudson River Craft Beer Festival

Held at the tail end of summer, Beacon’s Hudson River Craft Beer Festival lets you sample dozens of different craft brews from around the Hudson Valley and across the entire region. Of course there are also food vendors and local musicians providing a soundtrack for the popular event. The location, in Beacon’s Riverfront Park, couldn’t be better. 

Hudson Valley Hot-Air Balloon Festival 

About 15 miles east of Poughkeepsie, the Hudson Valley Hot-Air Balloon Festival is well worth the drive. The popular event — held for more than three decades — features dozens of hot-air balloons filling the sky. If you want to be a part of the spectacle, reserve ahead of time for a thrilling ride over the Hudson Valley. Stick around after sunset, when the glowing balloons are an unforgettable sight.

Hudson Valley Shakespeare Festival

All summer long, the Hudson Valley Shakespeare Festival brings world-class productions of the Bard’s plays, including the most famous ones (“Romeo and Juliet” and “Macbeth”) and the most obscure (“Cymbeline” and “Troilus and Cressida”). And there are also productions of thrilling new works like a post-apocalyptic take on “The Simpsons” called “Mr. Burns: a Post-Electric Play.” The festival has moved to a 98-acre property in Garrison where it will perform under a tent until it finishes construction on its new open-air theater.

Hudson Valley’s Best Events in Fall

Because the maple trees have changed to vivid shades of red and orange, this is one of our favorite seasons in the Hudson Valley. The crowds thin out a bit, but you still should get tickets in advance for popular events like Croton-On-Hudson’s Great Jack-O-Latern Blaze.

Great Jack-O-Lantern Blaze

Halloween is a big deal in the Hudson Valley. That’s why thousands of people turn out every year for the season’s biggest and brightest event, the Great Jack-O-Lantern Blaze. Held in Croton-On-Hudson, it sets the grounds of the 17th-century Van Cortland Manor ablaze with color and light. Hand-carved pumpkins are arranged into elaborate displays, including a massive gateway that casts an eerie glow on the proceedings. This is definitely a kid-friendly event.

Sheep and Wool Festival 

Just when the weather starts to get a bit chilly, Rhinebeck’s Sheep and Wool Festival arrives to make you feel all warm and cozy. There’s plenty for sale here, from expertly crafted sweaters, blankets, and other items to hand-dyed wools and everything else you need to make your own masterpiece. For the kids, there’s a parade, a petting zoo, and a chance to take a selfie with a llama or two. It all takes place at the Dutchess County Fairgrounds.

Hudson Valley’s Best Events in Winter

Just because the temperatures drop doesn’t mean residents stay indoors. There are plenty of winter activities that are worth braving the cold for.

Celebration of Lights

Poughkeepsie’s Dongan Square Park is decorated with thousands of flickering lights for the annual Celebration of Lights, which turns the area into a winter wonderland. This isn’t your usual holiday event, because you’re more likely to hear the sounds of bagpipes than sleigh bells. The evening ends with a tremendous fireworks display.


The holiday celebration that is Sinterklaas is steeped in the old Dutch traditions from way back when the settlers of the Hudson Valley hailed from the Netherlands. The celebration spans over two weekends kicking off on the last Saturday in November with a boat setting sail from Kingston. There is a children’s parade, puppet show, lots of music and a hearty celebration of  the coming winter season. The fun continues in Rhinebeck the first Saturday in December with a parade, shows, puppetry at the highest level and festive music and events throughout the day. It is a not to be missed event if your calendar is open!

Hudson Valley’s Best Events in Spring

Peekskill Cherry Blossom Festival

Although you never need an excuse to meander along Peekskill's Riverfront Walkway, why not visit when more than 100 cherry trees start to bloom? The Cherry Blossom Festival, sponsored by Peekskill's Rotary Club, celebrates nature's bounty as well as community. Expect to find food vendors and a multitude of children’s activities.