November 20 – December 11 Saturdays: Limar's Farmer Market Craft Fair.
Lagrangeville.
November 20 – December 19, Weekends: Newburgh Market's Holiday Pop Up Shop.
Newburgh.
November 21: 38th Annual Holiday Craft Fair. Hopewell Junction.
November 22 – December 27, Mondays: Sullivan 180 Walkthrough Mondays at Peace, Love& Lights. Bethel.
November 24: Rudolph the Red-Nosed Reindeer. Poughkeepsie.
November 25 – December 29: Fortis Christmas Lights for a Cause Brielle Grace BreastCancer. Fishkill.
November 25: Ninth Annual Turkey Trot. Kingston.
November 25 – December 12, Thursdays-Sundays; December 16 –December 26: The Wonderland of Lights. Rhinebeck.
November 26 – December 24. Santa is Coming to Town! Middletown
November 26 – December 24. Visit Santa 2021 at Poughkeepsie Galleria. Poughkeepsie
November 26 – December 19, Fridays – Sundays: A Frosty Fest. Ulster Park.
November 26 – December 30: Bruschi Christmas. Wallkill.
November 26 – December 19, Fridays – Sundays; Dec. 22 & 23: Catskill Christmas Express. Kingston.
November 26 – December 25: ERDAJT'S Holiday Light Display. Lagrangeville.
November 26: Holiday Kickoff with Santa. Highland.
November 26 – December 23, December 26: Holiday Lights in Bloom. Montgomery.
November 26 – December 19, Saturdays & Sundays: Holiday Mansion Tours.
Poughkeepsie.
November 26 – December 19: Holiday Market at Bethel Woods. Bethel.
November 26 – December 29, Closed December 25: Winter Wonderland. Staatsburg.
November 26 – December 26, Fridays – Sundays: Kevin McCurdy's Holiday Spirit Festival. Wappingers Falls.
November 26 – December 26: Watt Christmas Wonderland. Goshen.
November 27 – 28: Brookmeade Holiday Craft Fair. Rhinebeck.
November 27: The Great Inflate. Pawling.
November 27: Holiday Small Business Pop-Up Shoppe. Newburgh.
November 27: Annual Tree Lighting and Light Parade. Wappingers Falls.
November 27 & Dec. 11: Let’s Wrap, Beacon! Beacon.
November 28: HVArt Market Makers Market. Poughkeepsie.
November 28. Holiday Kick-off with Santa. Poughkeepsie.
December 2:
Eileen Ivers: A Joyful Christmas. Bethel.
December 2: Morgan James: A Very Magnetic Christmas Tour. Pawling.
December 2:
Orchestra 914 Holiday Concert at the Paramount.
Peekskill.
December 3 – December 24. Photos with Santa. Newburgh
December 3 – 4, 9 – 10, 16 – 18: Dinner With Santa. Bethel.
December 3: Handel's MESSIAH. Beacon.
December 3: Snowflake Festival. Kingston.
December 4 – 5, 11 – 12, 18: Breakfast with Santa 2021. Bear
Mountain.
December 4: Brunch with Santa. Poughkeepsie.
December 4: Christmas Craft Fair. Wallkill
December 4: Holiday Artisan Market. Highland Falls
December 4: The Grand Illumination. Lagrangeville
December 4 – 5, 11 – 12: Christmas in the Village. Monroe.
December 4 – 5: Dutchess Handmade Pop-Up Shop. Poughkeepsie.
December 4 – 5: Rock This Town Orchestra Christmas Spectacular. Pawling.
December 4 – 5, 11 – 12. Christmas in the Village. Monroe.
December 4: Santa Landing By Helicopter in the Village of Monroe!
Monroe.
December 4: Sinterklaas. Rhinebeck.
December 4: Wreath Making Class. Chester.
December 4: Photos At Santa's Workshop. Fishkill.
December 4: Selfies with Santa. Walden
December 4 – 5: The Nutcracker. Hopewell Junction.
December 5: Beekman Fire Company Cookies with Santa Event. Poughquag.
December 5: Handel's MESSIAH in Brewster. Brewster.
December 5: Sinterklaas Day and Dutch Holiday Traditions Children's Program.
Wappingers Falls.
December 5: Stars of La Cage presents: The Edwards Twins- Christmas with the Stars. Peekskill.
December 5. Breakfast with Santa. Hopewell Junction.
December 5. Annual Holiday Open House. Hopewell Junction.
December 5. Santa Cares Events Sensory Friendly Event Galleria at Crystal Run. Middletown.
December 5. Welcome Santa Party. Newburgh.
December 5. Sweet Treats with Santa. West Point.
December 5. Holiday Vendor Fair. Walden
December 6. Pet Photo Nights at Poughkeepsie Galleria. Poughkeepsie.
December 11. Kids' Holiday Paint Party. Newburgh.
December 11. Children's Holiday Craft Workshop. Fishkill.
December 11: 3rd Annual Breakfast with Santa. Wappingers Falls.
December 11: SANTA PAWS ~ Pet photos with Santa.
Pine Bush.
December 11: Socially Distant Santa and Mrs. Claus. Pawling.
December 11: Holiday Puppet Show. Hudson.
December 11: Gingerbread House Party. Warwick.
December 11: Sugar Loaf Holiday Celebration. Sugar Loaf.
December 12: Cirque Musica Holiday Spectacular. Poughkeepsie.
December 12. Brunch with Santa. Highland.
December 12. Santa Cares Events Sensory Friendly Event at Poughkeepsie Galleria. Poughkeepsie.
December 13: Holly Jolly Gingerbread Houses. Poughkeepsie.
December 13. Pet Photo Night at Galleria at Crystal Run. Middletown.
December 13. Pet Photo Nights at Poughkeepsie Galleria. Poughkeepsie.
December 17: Film: The Nightmare Before Christmas (1993).
Poughkeepsie.
December 17: The Nightmare Before Christmas. Kingston.
December 18: A Dickens Tale. Rhinebeck.
December 18 – 19: Annual Santa Brunch. Lagrangeville.
December 18: Handel's Messiah. Poughkeepsie.
December 18: Holiday Craft Fair. Poughkeepsie.
December 18: SLAMBOVIAN CIRCUS OF DREAMS: "AVery Slambovian Christmas". Beacon.
December 18 – 19. Annual Santa Brunch. Lagrangeville.
December 19: Brunch with Santa. Carmel.
December 27 – 30: Holiday Family Camp. Claryville.