The Inside Press

Magazines serving the communities of Northern Westchester

Holiday Stroll

Chappaqua’s Always Magical HOLIDAY STROLL on December 3rd: Ice Sculpting, Tree Lighting, Horace Greeley Encords… and More!

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The annual Holiday Stroll is back in Chappaqua December 3! Memory making and heartwarming activities for the whole family! Discover a host of shops, new and old favorites! Whether you celebrate Christmas, Hanukkah or Kwanzaa, or just wish to embrace the spirit of the season, you do not want to miss this! 

December 2022, Chappaqua, NY –  It’s the most magical time of year again and the annual Holiday Stroll is back! The holidays come alive in this charming hamlet; this is the perfect time for families to enjoy a festive day in downtown Chappaqua. 

This year’s Holiday stroll on December 3 will feature a meet and greet with Santa Claus bringing cheer to all and posing for pictures with little ones from 2 to 4 p.m. 

Experience a live ice sculpting presentation in front of Desires By Mikolay at 3 p.m., where you can watch master carvers create two holiday themed carvings out of giant blocks of ice using nothing but chainsaws. This is a decade long tradition you have to see for yourself!

Festivities continue at 4:30 p.m. at the New Castle Historical Society where you can enjoy the sounds of Holiday-themed Carols by Horace Greeley Encords and witness a festive Christmas tree lighting with thousands of twinkling lights.

Enjoy the charm of downtown Chappaqua as you pop into local shops, discover new merchants, checkout the latest fashions, shop local for holiday gifts, and pick up all the necessary essentials this gift-giving season. 

If you are worried about the cold, we got you covered! There will be a complimentary food truck from the Chamber of Commerce serving up Hot Cocoa and apple cider donuts to make sure everyone is warm and toasty.

Chappaqua’s Holiday Stroll will be on December 3, from 2 p.m. – 6 p.m. throughout downtown Chappaqua. 

In addition, save the date December 18 for more holiday festivities in town including a December 18th Menorah Lighting and bonfire!

News courtesy of the Chappaqua Millwood Chamber of Commerce, Desires by Mikolay and the New Castle Historical Society

Festive Stroll of Holiday Homes: November 22 and 23

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The Ossining Children’s Center (OCC) will be the beneficiary of the Festive Stroll of Holiday Homes, Friday, November 22 and Saturday, November 23, 2019. The event is produced in partnership with Holbrook Cottage, a lifestyle shop located in Briarcliff Manor.

The Festive Stroll, founded 21 years ago by Sue Taub of Holbrook Cottage and of Briarcliff Manor, will feature decorating traditions from around the world that will be displayed in three Sleepy Hollow homes. In addition to the magnificent decorations, the Stroll will highlight the rich history of the Philipse Manor neighborhood.

Two of the classic homes, both built in the 1920’s, will whisk strollers away to countries around the world through creative table settings, unique floral displays, and Christmas trees decorated in styles representing various cultures. Guests will travel from the British Isles, to Scandinavia, to Latin America, experiencing a rich tapestry of global Christmas traditions.

Thanksgiving will also be celebrated along the Stroll in a home that will become the true expression of a harvest bounty. Abundant displays of flowers and gourds will give visitors wonderful ideas to take home for their very own Thanksgiving celebrations the following Thursday!          

Guests will also experience Hanukkah through children’s eyes, in a whimsically decorated playroom featuring games and songs. The room will be punctuated with an eclectic display of menorahs, encompassing many styles and traditions.

On Friday, November 22, there will be a Festive Stroll Benefit Luncheon at the Sleepy Hollow Country Club, located in Scarborough, NY. Throughout the weekend, small festive touches will entice guests into the holiday spirit. Victorian carolers and a jovial holiday display will greet shoppers as they enter Holbrook Cottage to browse through the distinctive decorative items available for purchase. “The Stroll is an immersive holiday experience attracting revelers from as far as Eastern Connecticut and Southern New Jersey,” said Festive Stroll committee chair Clorissa Gioscia of Briarcliff Manor. “This year promises to be bigger and better than ever.”

All Festive Stroll proceeds will go to the Ossining Children’s Center’s Tuition Assistance Fund. OCC’s tuition program provides quality educational child care to children here regardless of their families’ incomes. Each year the Center enables more than 100 low- and moderate-income parents to maintain steady employment and to model a positive work ethic for their children. During their time at OCC children gain the skills and tools they need to succeed in school and in life. OCC instills a strong foundation enabling every child to reach their full potential. For more information about tour times and destinations and ticket purchase options for the Festive Stroll of Holiday Homes call the Ossining Children’s Center at 941-0230, ext. 22. Also be sure to visit ossiningchildrenscenter.org