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Top 10 Dutchess Events in December

Date Published: November 20, 2023

With spirits soaring and holiday cheer all around, December truly is an enchanting time of year in New York’s Hudson Valley. Here in Dutchess County, there are plenty of attractions throughout Dutchess County that will warm your heart and brighten your day.  

The annual Sinterklaas Festival in Rhinebeck is always a big hit with the youngsters (and the young at heart!), and many Dutchess County historic sites will be all decked out for special holiday tours and festive events. If you’re searching for unique, handmade gifts for your family and friends, grab your holiday shopping list and head straight to one of Dutchess County’s many holiday craft fairs.

Plus, in honor of the 75th anniversary of the Universal Declaration of Human Rights — which Eleanor Roosevelt helped write for the United Nations — the Franklin D. Roosevelt Presidential Library and Museum will host a a celebration of human rights on Dec. 10  that will include several presentations, a panel discussion and a concert. Click here to see a schedule of that day's events.

Here’s a look at some more can’t-miss Dutchess experiences in December. Get your camera ready! And if you’d like to share your pictures, click here and tag @dutchesstourism.com on social media. 

Boyce Park, Wingdale
Boyce Park, Wingdale

Holiday Festivals and Lights Displays 

• Wonderland of Lights (Select nights, Nov. 22 – Dec. 30 at the Dutchess County Fairgrounds, Rhinebeck) — This drive-through lights extravaganza features dozens of spectacular exhibitions and musical accompaniment. Be sure to ask about enchanted 3D elf glasses available for purchase at the gate.

• Kevin McCurdy’s Holiday Spirit Festival (Fridays, Saturdays and Sundays, Nov. 24 through Dec. 23 at Bowdoin Park, Wappingers Falls) — If you thought Kevin McCurdy’s Haunted Mansion was fun, be sure to check out his Holiday Spirit Festival! Experience more than 15 attractions on your Winter Wonderland Walk.

• ERDAJT Holiday Light Display (Nightly from Nov. 24 – Dec. 28 at 8 Patrick Drive, LaGrangeville) — A holiday tradition for the Gay Family since 1995 (ERDAJT are the initials of the family’s three children), this attraction set a Guinness World Record in 2014 and seems to get bigger every year. This season’s display features 720,426 lights, 1,700 strobes and 255 songs!  

• Town of LaGrange Festival of Lights Parade (Saturday, Nov. 25, 3:30 p.m. on Route 55, LaGrange) — This annual event kicks off the holiday season and features fun floats and lighted firetrucks and highway trucks. Stick around for a photo op with Santa and Mrs. Claus in Lexington Plaza following the parade.

• Pine Plains 38th Annual Town Decorating Day and Parade of Lights (Saturday, Nov. 25, beginning at 3 p.m. in Pine Plains) — Help decorate the Christmas trees that line the sidewalks, visit with Santa, listen to holiday music playing through the town center, and enjoy cookies and cocoa. The parade begins at 5 p.m.

• Photos with Santa (Beginning Thursday, Nov. 30, 2 p.m. at the Poughkeepsie Galleria) — Head to the center court to see Santa in front of a new display. Special events include Sensory Santa on the morning of Dec. 3; Breakfast with Santa on Dec. 10 at 10 a.m.; and Pet Night with Santa on Dec. 4, 12 and 18.

• Inaugural Akindale Holiday Tree Lighting (Thursday, Nov. 30, 4:30 – 7 p.m. at Akindale Farm, Pawling) — Be sure to register now for this free community event, as space is limited.

• Millbrook Parade of Lights (Friday, Dec. 1, 3 p.m. on Franklin Avenue, Millbrook) — Stop in and see Santa at the Angels of Light office (RSVP required) before the kids’ Electric Mini-Vehicle Brigade at 5:45 p.m. and the Parade of Lights at 6 p.m.

• City of Poughkeepsie Holiday Tree Lighting (Friday, Dec. 1, 7 p.m. at Dongan Square Park, Poughkeepsie) — Mayor Marc Nelson and Mayor-Elect Yvonne Flowers will be in attendance. A holiday tree at Mural Square also will be lit in advance.

• The Grand Illumination (Saturday, Dec. 2, 4:30 – 6 p.m. at Tymor Park, Union Vale) — Scenic Tymor Park will blaze forth with colorful holiday lights at this annual event. Make s’mores around the fire pits, visit with Santa, receive a special handcrafted ornament and some magical reindeer food to take home. The display will light up each night thereafter through Christmas.

• Town of Dover Holiday Fest and Christmas Tree Lighting (Saturday, Dec. 2, 6 p.m. at Boyce Park, Wingdale) — The annual lights exhibit is all set up in advance of the big Christmas tree lighting on Dec. 2. The park is open until 8 p.m. each night for anyone wishing to stroll through the display.

• Sinterklaas Festival (all day Saturday, Dec. 2, in Downtown Rhinebeck) — The streets of Rhinebeck are filled with music and cheer, laughter and innocence, as the entire community rallies around its children in observance of an ancient tradition rooted in the Hudson Valley’s rich history as a Dutch colony.

• Arlington Holiday Festival (Saturday, Dec. 2, 12 – 4 p.m. on Raymond Avenue, Poughkeepsie) — This afternoon of festivities includes an Egg Nog Crawl, horse-drawn carriage rides, live entertainment, a petting zoo, BeeBee the Clown, and a parade and caravan. 

• Pleasant Valley Festival of Lights Parade (Saturday, Dec. 2, 6:45 p.m. on Main Street, Pleasant Valley) — The parade features the third annual float competition; stop in and see Santa in the upper Town Hall parking lot.

• Decemberfest (Friday and Saturday, Dec. 8 and 9, 4 – 8 p.m. at Eastdale Village, Poughkeepsie) — Enjoy two incredible evenings of savings and promotions at participating businesses in Eastdale Village. Also, free photos with Santa on Dec. 8 from 1 – 4 p.m.

• Town of East Fishkill Menorah and Tree Lighting (Saturday, Dec. 9, 5 p.m. at the East Fishkill Community Center) — Celebrate the holiday season with the entire community!

• Rhinecliff Festival of Lights (Saturday, Dec. 9, 5 p.m. in downtown Rhinecliff) — Enjoy a complimentary cup of hot cocoa from The Epicurean and a holiday cookie from Kips Tavern as you stroll through the streets lined with luminaria.

• Rhinebeck Menorah Lighting & Chanukah Party (Saturday, Dec. 9, 6:30 p.m. at the Rhinebeck Menorah on East Market Street) — Following the lighting, enjoy dinner and arcade fun at the Rhinebeck Jewish Center on Montgomery Street. Email RSVP@RhinebeckJewishCenter to RSVP.


Related: Dutchess Tourism's CIA Chef Finder digital passport


White House Dinner 

Friday, Dec. 1, 5:30 – 9:30 p.m. at the Vassar College Alumnae House, Poughkeepsie  

Former White House Chefs Guy Mitchell and Michael "Woody" Raber — both of whom trained at the Culinary Institute of America — present an evening of storytelling, live cooking demonstration and an exquisite, Presidential-themed dinner. The menu will be prepared by renowned Hudson Valley chef Bruce Kazan of Main Course Catering. Click here to RSVP. If time allows, arrive at the Vassar campus early and swing by the Frances Lehman Loeb Art Center to see more than 22,000 works of art, including Kara Walker’s “Testimony” exhibit, which features a collection of black, cut-paper silhouettes which depict the violence and sexual exploitation inflicted by white American enslavers on the Black people they enslaved. “Testimony” will be on display through Dec. 22. 


Happy Valley Arcade Bar, Beacon
Happy Valley Arcade Bar, Beacon

Pet Photos with Santa 

Saturday, Dec. 2, 12 – 3 p.m. at Happy Valley Arcade Bar, Beacon 

Santa Claus will certainly be busy in the weeks leading up to Christmas Eve, but he will be taking time out of his hectic schedule to pose for pictures with some four-legged friends in Happy Valley Arcade Bar’s outdoor courtyard. Click here for details. Inside Happy Valley, you’ll find more than two dozen fully operational vintage video game consoles, including Missile Command, Donkey Kong, Pac-Man and Space Invaders, as well as several vintage pinball machines. Happy Valley features a well-stocked bar featuring a full assortment of beer, wine and spirits — including some locally produced favorites like Beacon Bourbon, Great 9 Gin and Earl Grey Vodka from Denning’s Point Distillery in Beacon, and Tod and Vixen Gin from the Vale Fox Distillery in Poughkeepsie, as well as beer from Sloop Brewing in Hopewell Junction, Industrial Arts Brewing in Beacon, the Hudson Valley Brewery in Beacon, and the Mill House Brewing Company in Poughkeepsie — along with some tasty bites. 


Northern Dutchess Symphony Orchestra’s “Winter Wonderland” 

Saturday, Dec. 2, 3 p.m. at FDR High School, Staatsburg 

Guest conductor William Stevens leads the Northern Dutchess Symphony Orchestra in its Sounds of the Season holiday concert. The evening’s program features selections from Bizet and Tchaikovsky, from “Harry Potter” and “Frozen,” and, of course, plenty of holiday favorites. Click here to purchase tickets, and be sure to check out other concerts on the NDSO’s 2023-24 schedule, which picks up after the new year and continues through the spring.   


The Academy, Poughkeepsie
The Academy, Poughkeepsie

Drag Holiday Events 

• "A Hard Candy Holiday" Drag Brunch (Sunday, Dec. 3, 11 a.m. at the Academy, Poughkeepsie) — Hostesses Victoria Bohmore and Shawnna Alexander present a hilarious holiday-themed drag event like no other. Enjoy brunch and bottomless mimosas as you watch performances by Ganivah Cache Diamond, Cookie Doe, Fantasia Fae and Katie D. Lite. The Academy is a fantastic, multi-faceted venue in the heart of downtown Poughkeepsie.  

• Sherry Vine in "Oy to the World" (Sunday, Dec. 10, 6 p.m. at Reserva Wine Bar, Beacon) — Be sure to wear your most festive holiday attire as Sherry Vine presents her holiday show full of naughty humor, gorgeous costumes and bawdy banter. Choose between the 12 p.m. brunch show or the 6 p.m. evening tapas show. Built in a former laundromat, Reserva’s interior highlights the building’s original design from 1895 with its original floors and exposed brick walls and presents a quaint, sophisticated event space.   


Holidelic Holiday Funk Revue, photo courtesy of Mikiodo
"Holidelic" Holiday Funk Revue (photo courtesy of Mikiodo)

"Holidelic" Holiday Funk Revue 

Fridays and Saturdays, Dec. 8, 9, 15 and 16, 8 p.m. at Kaatsbaan Cultural Park, Tivoli 

Grammy Award-nominated vocalist and percussionist Everett Bradley puts the funk in your holiday season with the “Holidelic” holiday funk revue in Kaatsbaan's indoor Black Box Theater. Bradley takes on the role of Papadelic, Funk’s Father Christmas, who is an amalgamation of George Clinton and Santa Claus and, with a talented ensemble of musicians, will transport you to a world where funk meets holiday joy. Click here to purchase tickets. Bradley has worked with an assortment of iconic musicians, including David Bowie, Bon Jovi, Bruce Springsteen’s E Street Band, Hall and Oates and Carly Simon. He was even the subject of one of Rolling Stone’s “Unknown Legends” interview series in 2021.  


Related: Interact With Indigenous Culture in Dutchess County


The Pawling Concert Series Welcomes the Vivaldi Project 

Friday, Dec. 15, 8 p.m. at the All Saints’ Chapel, Trinity-Pawling School, Pawling 

Get ready to step back in time through music to the 17th and 18th centuries, as the Pawling Concert Series presents the Vivaldi Project, an instrumental ensemble that pays homage to influential Italian composer Antonio Vivaldi for his pivotal position between earlier Baroque and later Classical composers. In addition to familiar string instruments, the Vivaldi Project ensemble will incorporate harpsichord and theorbo, as well as a vocalist, for this performance. Click here to listen to recordings of the ensemble and to purchase tickets for this concert. After this show, this 50th season of the Pawling Concert Series will pick up again in the spring with two more sensational shows at the Trinity-Pawling School. 


Maxon Mills, Wassaic
Maxon Mills, Wassaic

Wassaic Project Winter Art Exhibition Opening 

Saturday, Dec. 9, 3 – 5 p.m. at Maxon Mills, Wassaic 

The Wassaic Project presents the opening of its winter art exhibition, titled “I Should Have Been a Pair of Ragged Claws,” in its Maxon Mills gallery. Maxon Mills is an historic, seven-story wooden grain elevator along the train tracks that has been repurposed into a uniquely magnificent venue for contemporary artists of all types to show their work. “I Should Have Been a Pair of Ragged Claws” will be on display through March 16, and the gallery is open Saturdays from 12 – 5 p.m. Click here to see a list of the featured artists. While you’re in Wassaic, be sure to walk across the street to The Lantern for a delicious meal and a beverage or two. 


The Bardavon 1869 Opera House, Poughkeepsie
The Bardavon 1869 Opera House, Poughkeepsie

“A Celtic Christmas” by A Taste of Ireland 

Saturday, Dec. 16, 7:30 p.m., and Sunday, Dec. 17, 3 p.m. at the Bardavon 1869 Opera House, Poughkeepsie 

Award-winning Irish musicians complement the world’s best Irish dancers in this high-energy celebration of an Irish Christmas. Featuring a powerful combination of traditional music and classic holiday carols, “A Celtic Christmas” is a spectacular and festive program that will set your holiday spirit soaring. A Taste of Ireland is led by Brent Pace — an Irish dancer for more than 20 years with six national titles to his credit — and Ceili Moore — whose competitive Irish dancing career includes national and world championships. Click here to reserve tickets. If time allows, make a weekend out of it! The Bardavon 1869 Opera House is within walking distance of a host of great restaurants, as well as the Poughkeepsie Grand hotel. 


Shadows on the Hudson, Poughkeepsie
Shadows on the Hudson, Poughkeepsie

Christmas Eve Brunch with Santa 

Sunday, Dec. 24, 10:30 a.m. - 2 p.m. at Shadows on the Hudson, Poughkeepsie 

Mere hours before he climbs aboard his sleigh and takes to the sky with his reindeer, Santa Claus will be fueling up for his around-the-world trip at Shadows on the Hudson, an award-winning restaurant perched on a cliff overlooking the Hudson River. Enjoy a delicious brunch, along with Shadows’ extravagant mini-dessert display. Keep those cameras handy for photo ops. Click here to make reservations. 


Bannerman Castle, Pollepel Island, Beacon
Bannerman Castle, Pollepel Island, Beacon

Bonus Event 

Summer Dreams... in December 

It’s never too early to start planning your summer excursions, and several of Dutchess County’s most popular summer attractions are already gearing up for next season. Tickets are available for these events and would make wonderful holiday gifts: 

• Hudson Valley Renegades (Wappingers Falls) — The Renegades minor-league baseball team plays 66 home games each season at Heritage Financial Park (formerly Dutchess Stadium). The High-A affiliate of the New York Yankees, the Renegades made their first playoff appearance since 2019 last year, reaching the South Atlantic League Championship Series. Six former Renegades made their Yankees debuts in 2023, including Anthony Volpe and Jasson Dominguez. Season ticket packages are available for the 2024 season, as are Pick 6 Mini Packages.

• SplashDown Beach (Fishkill) — “America’s Biggest Little Water Park” features water slides and attractions for all ages. Get your pulse racing on the Humunga Half-Pipe (New York’s only zero-gravity half-pipe) or The Megalodon raft ride. Relax and cool off as you float down the Croc Creek Wavy Lazy River in your own tube. The Pelican Bay Water Playground opened in 2023 with four new water slides and a 500-gallon dumping bucket. Discounted season passes for 2024 are available.

• Bannerman Castle (Beacon) — The ruins of this Scottish-style castle on Pollepel Island in the Hudson River are truly a sight to behold. Built by military surplus dealer Frank Bannerman in the early 1900s, the castle, the adjacent residence and the surrounding gardens are all being painstakingly restored by the Bannerman Castle Trust. Special events like musical and theatrical performances, movie nights, lectures and themed dinner events are popular attractions on the island, which is easily reachable aboard the Estuary Steward tour boat or your own kayak or canoe. Tickets are on sale now for the 2024 cruise and walking tours of the island, which pick up again in April.

• Old Rhinebeck Aerodrome (Red Hook) — Hold onto your hats for this thrilling experience high above the Hudson River! Schedule a flight in an authentic 1929 open-cockpit biplane and look down from above upon the many scenic wonders of the Hudson Valley. The half-hour Lighthouse Tour offers breathtaking views of Hudson River lighthouses (including the Saugerties Light, the Rondout Light, and the Esopus Meadows Light) and Gilded Age mansions, along with all the natural beauty of the river and the surrounding Taconic, Berkshire and Catskill mountains. You'll want to keep your camera handy for this! Shorter biplane rides are also available. Flights run from May through October. Schedule your reservation for next year now and take advantage of the 2023 rates.

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