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Memorial Day Weekend 2023 in Westchester: Festivals, Day Trips, and More Things To Do

Splash, slide and cool off at Legoland's Water Playground, which makes a splash with its Memorial Day weekend debut. Photo courtesy of Legoland
Splash, slide and cool off at Legoland's Water Playground, which makes a splash with its Memorial Day weekend debut. Photo courtesy of Legoland
5/24/23 - By Katherine Dhurandhar

Looking for the best things to do in Westchester and the Hudson Valley this weekend? Here are some family-friendly events and activities to add to your list for this long holiday weekend.

If you're staying in town for Memorial Day weekend, there's no shortage of fun things to do. Celebrate the beginning of summer with the opening of Westchester beaches and local water parks. The long-awaited Legoland New York Water Playground is also set to debut.

Many local towns and villages celebrate Memorial Day weekend with parades and ceremonies, including an antique car show in Bronxville and a special changing of the flag ceremony on the beautiful Walkway Over the Hudson. Also on our radar are historical celebrations, including a commemoration at St. Paul's Church and a World War II tribute at the FDR Library.

Several seasonal, late-spring festivals take place this weekend, including the Sons and Daughters of Italy Festival, the Chestnut Ridge Sheep and Wool Festival, and the Woodstock-New Paltz Arts and Crafts Fair.

Don't miss our reviews of the best things to do in Westchester and the Hudson Valley, including spring day trips, nearby swimming lakes, and strawberry picking farms.

More Things To Do in Westchester this Week with Kids

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Enjoy the food, fun, and fireworks at the Sons and Daughters of Italy Festival all weekend long. Photo courtesy of the event
Enjoy the food, fun, and fireworks at the Sons and Daughters of Italy Festival all weekend long. Photo courtesy of the event

Things To Do in Westchester This Weekend With Kids

Sons and Daughters of Italy Festival

Wappingers Falls–FREE
Thursday, May 25-Sunday, May 28
Enjoy carnival rides, a craft fair, and food vendors at this annual, family-friendly festival held over Memorial Day weekend. Visit the all-new garden and entertainment tent. Visit on Sunday night to catch the annual fireworks show. READ MORE

Legoland New York Water Playground Opening Week

Goshen
Opens Saturday, May 27
Splash, slide, and cool off with Lego friends and pirates at the Legoland Water Playground, featuring waterslides, a giant water dump bucket, and a build-your-own area to make Lego boats to float and race. READ MORE

Westchester Beaches Open

Multiple Locations
Saturday, May 27
Westchester County beaches, including Glen Island Park in New Rochelle; Playland Park in Rye; and Croton Point Park in Croton-on-Hudson, begin their pre-season schedule.  READ MORE

Weekend Storytime

Rye
Saturday, May 27-Sunday, May 28
The Westchester Children's Museum invites visitors to enjoy a special storytime every weekend for visitors of all ages. In May, stories and picture books celebrate AAPI Heritage. READ MORE

WWII Military Displays

Hyde Park–FREE
Saturday, May 27-Sunday, May 28
This Memorial Day tribute features a display of military artifacts from World War II taking over the lawn of the FDR Library. See period vehicles, costumed "soldiers," and D-Day-related exhibits which re-create a historic WWII encampment. READ MORE

Fairy House Hunt in the Garden

Poughkeepsie
Saturday, May 27-Sunday, May 28
Don your best wings and search the nooks and crannies of the Locust Grove grounds to find 30 hidden fairy houses on an enchanted walk. Check out some old favorites, as well as new houses created this year! A fairy-house map is your guide. READ MORE

Woodstock-New Paltz Art & Crafts Fair

New Paltz
Saturday, May 27-Monday, May 29
Held twice yearly—Memorial Day and Labor Day weekends—this fair showcases the work of more than 200 artists from across the United States. The children's tent features demonstrations and supervised arts and crafts projects. Live entertainment and activities are planned. READ MORE

Splashdown Beach Opening Weekend

Fishkill
Saturday, May 27-Monday, May 29
Get ready for wet and wild summer fun at America's biggest little water park. The park features water slides for all ages, a wave pool, lazy river, and toddler and baby water play areas. READ MORE

Sheep and Wool Festival

Chestnut Ridge–FREE
Sunday, May 28
Held under leafy shade trees in Chestnut Ridge, this family-oriented community event features child-friendly craft activities, a petting zoo, live music, local craft vendors, and delicious food. READ MORE

Memorial Day Sunset Changing of the Flag Ceremony

Poughkeepsie–FREE
Sunday, May 28
The Memorial Day flag-changing ceremony is the most special of the year. The sunset ceremony also includes a four-gun salute, the playing of "Taps," local artist Mary Kay Messenger performing "God Bless America," and a carnation toss into the Hudson River. READ MORE

Westmoreland Sanctuary Orienteering Meet

Mount Kisco
Sunday, May 28
Westmoreland Sanctuary partners with Hudson Valley twice a year to bring you a spring and fall orienteering meet. Orienteering combines the terrain of the outdoors with the thrill of a scavenger hunt. Navigate through Westmoreland’s woods, off-trail, using only a map and compass. Enter as an individual, family, or group! All ages and experience levels are encouraged. READ MORE

St. Paul's Church Memorial Day Commemoration

Mt. Vernon–FREE
Monday, May 29
St. Paul's Church hosts this Memorial Day ceremony. The day starts with a ceremony in the church and a tour of the historic cemetery as guests learn about the veterans buried there. READ MORE

White Plains Memorial Day Parade

White Plains–FREE
Monday, May 29
Local community organizations are invited to be "Patriots for a Day" and march in White Plains Memorial Day parade. A commemorative ceremony takes place in the cemetery at the parade's end. READ MORE

Yorktown Memorial Day Parade & Ceremonies

Yorktown Heights–FREE
Monday, May 29
Yorktown's Memorial Day celebrations include a service memorial located at the Town Hall followed by a parade, speeches, and ceremony at Jack DeVito Gazebo.  READ MORE

Memorial Day Parade and Antique Car Show

Bronxville–FREE
Monday, May 29
The annual Bronxville Village Memorial Day Parade rolls down Leonard Morange Square and leads to The Bronxville School, where ceremonial speeches and presentations are made. An antique car show follows.  READ MORE

Annual Memorial Day Races

South Salem–FREE
Monday, May 29
South Salem celebrates Memorial Day an annual slate of races, including 5K and 10K distances for adults, plus a Mile Fun Run. READ MORE

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