- 12/2 Sinterklaas Festival Day: Rhinebeck, NY
- 12/2 5PM – 9PM Tarrytown & Sleepy Hollow Winter Stroll
- 12/2 at 2PM TASH Holiday Market at Patriot’s Park
- 12/2 The Rivertown’s Chamber Presents the Holiday Trolley through Irvington, Dobbs Ferry & Hastings-on-Hudson, a shop local event *Tickets Required
- 12/6 Holiday Market at the Tarrytown Music Hall
- 12/6 – 12/17 White Plains Holiday Market
- 12/8- 1/1 Untermeyers Conservancy Grand Holiday Illumination: Yonkers, NY
- 12/10 White Plains Tree Lighting at Renaissance Plaza
- 12/11 Menorah Lighting at Cross County Center in Yonkers
Family Activities – Tickets Required
- 11/18 – 12/10 Boscobel Twilight Tours: Garrison
- 12/8 – 12/26 Mr. Dickens Tells a Christmas Carol at Lyndhurst
- Select Dates in November & December – Armour Stiner House Holiday Tour: Irvington, NY
Train Shows, Light Displays & Experiences – Tickets Required
- 11/9 – 1/7 LuminoCity Holiday Lights Festival: East Meadow, NY
- 12/9 & 12/10 Greenburgh Nature Center Holiday Train Show: Scarsdale, NY
- 11/17 -12/29 Polar Express Train Ride: Catskill Mountain Railroad
- 11/17 – 1/7 Bronx Zoo Holiday Light Display
- 11/17 – 1/13 NY Botanical Gardens Holiday Train Show *Consider NYBG “Glow” Light Display afterwards for additional fun!
- 11/24 – 12/31 Westchester’s Winter Wonderland Drive Thru Kensico Dam Plaza, Valhalla
- 11/25 – 12/23 Holiday Spirit Festival Winter Wonderland Walk: Wappingers Falls, NY
- 11/25 – 12/30 Wonderland of Lights Drive-Thru Dutchess County Fairgrounds
- 11/26 – 12/31 Holidays on the Hill Train Show: Somers, NY
Cut Down a Christmas Tree
- Battenfeld’s Christmas Tree Farm: Red Hook, NY (845) 758-8018
- Wilken’s Fruit & Fir Farm:Yorktown Heights, NY
- Fabulous Firs at Van Scott Farms: Poughkeepsie, NY
Museum Ideas/Indoor Activities
- Hudson River Museum: Yonkers, NY
- Westchester Children’s Museum: Rye, NY
- Sports Time USA: Ardsley, NY
- Legoland Discovery Center: Yonkers, NY
- Spins Hudson at the Factoria: Peekskill, NY
- Grand Prix: Mount Kisco, NY
- Wolf Conservation Center: South Salem, NY
- Maritime Aquarium: Norwalk, CT
- Adventure Aquarium: Camden, NJ
Ice Skating
- Bear Mountain Ice Rink (Opens 11/5) Tomkins Cove, NY For Skating Hours, FAQ’s & More, Click Here
- Cross County Center Pop-Up Rink (Open 11/19 – 1/1) Yonkers, NY For Skating Hours, FAQ’s & More, Click Here
- Brewster Ice Arena (Year Round) Brewster, NY For Skating Hours, FAQ’s & More, Click Here
- Playland Park Ice Casino (Year Round) Rye, NY For Skating Hours, FAQ’s & More, Click Here
Suggested Restaurants for Holiday Feels
- Goosefeather: Tarrytown, NY
- The Gingerman: Greenwich, CT
- Crab Tree’s Kittle House: Chappaqua, NY
- The Old ‘76 House: Tappan, NY
- Beekman Arms & Delamater Inn: Rhinebeck, NY
- Purdy’s Farmer & The Fish: North Salem, NY
- Olde Village Inne: Nyack, NY
- Mulino’s of Westchester: White Plains, NY
- Rolf’s of NYC: New York, NY
Weekend Trip Ideas
- Catskills, NY: Less than 2.5 hours from Westchester, the Catskills offer a myriad of winter activities such as skiing, snowmobiling, snowshoeing and more! For a full list of resorts/lodges, click here.
- Lake George, NY: Less than 3 hours from Westchester County. Good to visit December – March, but peak attraction time is in February (see below). Winter Carnival , Winter Realm , Dog Sledding, Snow Tubing, Sleigh Rides & More
- Stowe, Vermont: Less than 5 hours from Westchester County, Stowe is considered an Alpine Ski Capital of the East and ranked “Top 10 Ski Towns” by Forbes. Stowe is great to visit from December – March for winter activities such as ice climbing, dog sledding, fat biking, skiing and more!
Cozy Weekend Getaways
- Mohonk Mountain House Resort & Spa: New Paltz, NY
- Crystal Springs Resort: Sussex County, NJ
- Mirbeau Inn & Spa: Rhinebeck, NY
- The Abbey Inn & Spa: Peekskill, NY
- Castle Hotel & Spa: Tarrytown, NY