More Events:

November 01, 2022

Ride in a horse-drawn carriage and meet Santa in Chestnut Hill this holiday season

The festivities kick off on Saturday, Nov. 19 with Circle of Trees, a favorite among kids and families; visitors can also expect Santa sightings, straw mazes and live music

Holidays Shopping
Holidays on the Hill Courtesy of/Chestnut Hill Business District

Holidays on the Hill returns to Chestnut Hill from Saturday, Nov. 19 through New Year's Eve. There are plenty of special events for people of all ages to enjoy, including Circle of Trees on Nov. 19, Small Business Saturday on Nov. 26, the Holiday Garden Railway at Morris Arboretum from Nov. 25 through Nov. 30, Stag & Doe Nights on Wednesday evenings, Santa sightings and the neighborhood's annal holiday parade on Dec. 10.

Though some may say the holiday season doesn't begin until families have gathered for Thanksgiving dinner, others are already dreaming of bundling up, hanging stockings and singing along to classic carols. 

In the spirit of the impending season, Holidays on the Hill returns to Chestnut Hill on Saturday, Nov. 19, with special events running through New Year's Eve. Each event is free to attend, and there is something for people of all ages to enjoy. 

MORE: Stroll through a winter wonderland during Philadelphia Zoo's holiday light display

On Friday, Nov. 18, Chestnut Hill will be transformed into a winter wonderland, with seasonal and holiday decor on lampposts and in store windows in time for the festivities. The Chestnut Hill Business District, which includes more than 200 locally-owned shops and restaurants, offers plenty of options for Christmas shopping.

Chestnut Hill's Circle of Trees will be held on Saturday, Nov. 19, beginning at 5 p.m. A perennial favorite, the holiday season kick-off includes a visit from Santa, arriving on a fire engine to meet children and hear their holiday wishes. 

After dark, guests can listen to music and enjoy a straw maze while the neighborhood's trees are illuminated. 

From Friday, Nov. 25 through Dec. 30, Morris Arboretum is hosting the Holiday Garden Railway. Between 10 a.m. and 4 p.m. daily, visitors can view enchanting rail cars and decorated holiday villages spanning over a quarter-mile track with holiday lights and sounds. The event is free with admission to Morris Arboretum. 

After visiting the Holiday Garden Railway, celebrate Small Business Saturday on Germantown Avenue on Saturday, Nov. 26. Check off gifts from your holiday wish list while watching for Santa as he strolls throughout the neighborhood. You can also enjoy rides on a horse-drawn carriage from noon until 3 p.m. 

From 1 to 3 p.m., a Mummers trio and costumed Victorian carolers will entertain guests with holiday tunes and sing-alongs. 

Chestnut Hill's Stag and Doe Nights will return on Wednesdays starting Nov. 30 through Dec. 21. From 5 to 9 p.m., visitors can check out holiday entertainment, extended store hours, holiday specials and complimentary treats at stores along Germantown Avenue. 

Every Stag & Doe, from 6:30 to 8:30 p.m., shoppers can catch a glimpse of Santa strutting down the street to greet families while listening to a brass quartet. Also during that time, Stateside distillery will sell vodka and bourbon bottles with optional engraving at the Chestnut Hill Welcome Center, located at 8514 Germantown Ave.

Each Saturday in December from noon until 2 p.m., Santa will greet visitors at Market on the Fareway, located at 8221 Germantown Ave.

To wrap up the holiday season and prepare for the new year, the Chestnut Hill Community Association will hold its annual holiday parade on Saturday, Dec. 10. The parade begins at Chestnut Hill and Germantown avenues at 9 a.m. and concludes at 10 a.m. at Market at the Fareway. 

The Phillie Phanatic will also make an appearance, along with fire engines, marching bands, choirs, antique cars, horses and kids from participating local schools. The rain date is set for Saturday, Dec. 17. 

For more information about Chestnut Hill's holiday celebrations, check out the Chestnut Hill Business District's official website or Instagram

Holidays on the Hill

Nov. 19 through Dec. 31, 2022
Various days and times | Free
Chestnut Hill Business District
Philadelphia, PA 19119