It’s the most wonderful time of the year in Chestnut Hill! During Holidays on the Hill, visitors can immerse themselves in the spirit of the season by strolling through Philadelphia’s Urban Village.

Visitors can enjoy the tunes of a brass quartet, take a ride on a horse-drawn carriage along cobblestone streets, view an outdoor model train display, take advantage of late-night shopping hours, and experience encounters with Santa!

From Small Business Saturday to the legendary Stag & Doe Nights, Chestnut Hill is keeping beloved holiday traditions intact, while maintaining sensible COVID modifications to ensure that all visitors can celebrate safely.

Festival attractions include:

Circle of Trees

Saturday, November 20

A perennial favorite of local families and children, Chestnut Hill’s kick-off to the holiday season takes on a new COVID-friendly format this year, with Santa’s firetruck making stops at several neighborhood locations.  Stay tuned for more details about where he’s touching down.  

Small Business Saturday

Saturday, November 27

Check off everything on your list and support local businesses on the Hill! Shoppers are sure to find the perfect gift for loved ones this season in Chestnut Hill’s trendy boutiques and specialty shops.  Join classic Philadelphia mummers from 11 a.m.-2 p.m., costumed Victorian carolers from 1-3 p.m., Horse & Carriage Rides 12-3 p.m. and Santa Claus from 2-5 p.m. himself to experience the most magical shopping experience in the Philadelphia region!  

Stag & Doe Nights

Wednesdays December 1, 8, 15, 22

Chestnut Hill’s beloved annual Stag & Doe Nights return every Wednesday in December, featuring extended store hours, holiday specials, and complimentary refreshments at many stores.  Horse-drawn carriage rides on December 8 and December 22 from 6-9 p.m. and a brass quartet from 6:30-8:30 p.m. every Stag & Doe Night  help to create the seasonal atmosphere.  You may even catch a glimpse of Santa strutting down the Avenue and greeting families. In order to promote safety and avoid crowding, customers are encouraged to visit throughout the day to get a head start on shopping.

Garden Railway at Morris Arboretum 

The annual fan-favorite Holiday Garden Railway at Morris Arboretum, (100 E. Northwestern Avenue) returns on Thanksgiving weekend.

The exhibit features an intricate and expansive train display of 15 rails spanning a quarter-mile of the track, surrounded by natural materials, multiple train cars, towns, and miniature figurines. November 26 to January 2 from 10 to 4 p.m., along with weekend nightly tour hours.

Visit for more information.

Back By Popular Demand: Stateside Vodka Bottle Sales and Engraving.

Get in the Holiday “spirits” with fine locally-distilled vodka and bourbon from Stateside.  A fixture of Chestnut Hill’s Stag & Doe Nights for several years running, Stateside will be returning with bottle sales and personalized bottle engraving, all conveniently conducted at the Chestnut Hill Welcome Center at 8514 Germantown Avenue.  

Business and restaurant specials:

‘Tis the season for one-of-a-kind finds and specials. Visit throughout the season to check out offerings from Chestnut Hill’s fine shops and restaurants as they are announced.  

Other notes:


For the benefit of our customers, we are pleased to offer a special Free Parking promotion this holiday shopping season. The Chestnut Hill Parking Foundation is offering free parking in its six public lots all day and night every Wednesday between Thanksgiving and Christmas

Email any questions to

Thank You To Our Wonderful Holiday Sponsors

2021 Community Sponsors: