Whether you’ve lived in Rhinebeck your whole life or moved here recently, it’s no secret that our little town is full of family-friendly festivals. However, it can be confusing to know when, where and how these festivals are celebrated. Take a peek at this guide to all the little things Rhinebeck has to offer.
Car Show (May 3-4, 2025)
The Rhinebeck Car show is located in the Dutchess County Fairgrounds. This weekend event runs from 8am to 5pm and children 12 and under get in for free. The May 3rd show, happening on a Saturday, is the “Rod and Custom Dust Off”, dedicated to hot rods, street rods, customs, race cars, and compact customs/pickups. Sunday’s show is reserved for the unmodified antique cars and classic vehicles manufactured up to the year 2000. The Car show has hundreds of vendors, and typically hosts spectators from all over the northeast. There’s also a swap meet for car collectors that opens Friday at noon.
May Memorial Day Parade (May 26, 2025)
The Rhinebeck Memorial Day Parade is family-friendly and free to attend. The parade honors local veterans and their families, and takes place on a short walking path through the village. The parade passes through the town and the fairgrounds, pausing to raise the flag at the Village Hall, the Town Hall, the Doughboy statue across from the fire house, the post office, the cemetery, Legion Park and Legion Post #429. The parade begins at 10:30am on North Mulberry Street, and is typically over by 11:30.
Fourth Of July Parade (July 4, 2025)
For the Fourth of July, the town of Rhinebeck puts on a parade throughout the whole village. There are many different floats and groups that march in the parade, along with antique cars, trucks, motorcycles, farm equipment, and classic commercial vehicles. There’s music, marching bands, and plenty of candy thrown out to the crowd. Everyone is decked out in red, white and blue. And typically around 9:00 p.m., there are fireworks that can be viewed from the Walkway over the Hudson or even from Burger Hill.
Dutchess County Fair (Aug 19-24, 2025)
The Dutchess County Fair is full of fun for all ages. It celebrates agriculture and fun, providing local specialty foods and entertainment, as well as opportunities to interact with livestock. The fair is open from 10:00 a.m. to 10:00 p.m. Tuesday through Saturday, and closes at 8:00 p.m. on Sunday. Of course, there are the classic county fair rides and games, as well as over 1,000 vendors to explore. There are also fun activities like pig races, dock dog diving, and acrobatics, ensuring 6 days full of delightful activities.
Wine and Food Fest (Sep 6-7, 2025)
The Hudson Valley Wine and Food festival also takes place at the fairgrounds, and it offers a showcase for New York Wineries & Gourmet Specialty Foods. There are many other things to check out, like distilleries, hard ciders, a New York craft beers pavilion, and even a gourmet food truck corral. Visitors have many opportunities to learn about wine and food through cooking demonstrations. Similar to the fair, there are many lifestyle vendors, live entertainment, and food samples as well.
Oktoberfest (Sep 27-28, 2025)
The Handcrafted Oktoberfest is one of the nations top contemporary craft fairs. Spend a fall weekend exploring the many vendors and free activities set up, with multiple food trucks to choose from. Oktoberfest is at the Fairgrounds, and has many free demonstrations as well as live music and pumpkin-themed everything.
Sheep n’ Wool Fest (Oct 18-19, 2025)
Sheep n’ wool is the festival for all yarn-crafters and fiber-workers. There are plenty of yarn stores, selling a variety of sizes and colors, as well as hand dyed yarns. There are also live sheep, and the farmers demonstrate how to shear them. There is a room where they spin the wool into yarn, and an antique equipment auction. There are competitions, awards, kids activities, and workshops. And of course, there are many performers and foodstands, and events for all ages.
Halloween Parade (Oct 27, 2025)
The halloween parade is a way for people to show off their costumes before halloween. At 1:00 p.m., families walk through town to the Legion Hall, where kids get to parade around in age groups and win prizes on their costumes. There’s hot apple cider and doughnuts for participants, and it’s a fun experience for all.
Santa Sighting (Nov 22-Dec 24, 2025)
Head to the Poughkeepsie Galleria to spot Santa and get a picture! He and Mrs. Claus also often visit Rhinebeck village at the tree lighting ceremony at the village municipal parking lot. The festivities take place on a saturday in late november,, and starts at noon. Bring friends and family to take a picture in front of the tree, which is lit at 5:30 p.m.
