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! Guests can enjoy the holiday cheer of a brass quartet, take a ride on a horse-drawn carriage along cobblestone streets, view an outdoor model train display at Morris Arboretum, take advantage of late-night shopping hours and refreshments served at many of the local businesses and have their picture taken with our very own beloved Santa!  The historic charm of Chestnut Hill provides a nostalgic background for a holiday experience that harkens back to an earlier time.  Carolers will stroll the Avenue to add their music to the mood!

From Small Business Saturday to the legendary Stag & Doe Nights every Wednesday between Thanksgiving and Christmas, Chestnut Hill is rich with vibrant holiday traditions. 

Saturdays in December Santa will be at MARKET at the Fareway 12-2 p.m. Come visit him!

Festival attractions include:

Circle of Trees – November 19th

A perennial favorite of local families and children, Chestnut Hill’s kick-off to the holiday season will happen this year on November 19th, with Santa’s firetruck making stops at several neighborhood locations.  Stay tuned for more details about where he’s touching down and how you can join in for the enchanting annual illumination of trees at Woodmere Art Museum!

Small Business Saturday – November 26th

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

Stag & Doe Nights – November 30th & December 7, 14 & 21

Every Wednesday from Thanksgiving through Christmas.  Chestnut Hill’s beloved annual Stag & Doe Nights return, featuring extended store hours, holiday specials, and complimentary refreshments at many stores.  A brass quartet will roam every Stag & Doe Night from 6:30-8:30 p.m.  You may even catch a glimpse of Santa strutting down the Avenue and greeting families from 6:30-8:30pm. 

Woodmere Art Museum

Telling the stories of PHILADELPHIA’S Art and Artists.  Woodmere’s holiday store is open for in-person shopping again this holiday season! Find unique, one-of-a-kind, locally-made gifts for everyone on your Woodmere’s Museum Store also offers online shopping.  Stop in Closed on Tuesdays, Wednesdays through Friday’s 10am – 5:00pm, Saturday’s 10am – 6:00pm Sunday’s 10am – 5:00pm or schedule a private appointment with Museum Store Director Stephen Kerzner by calling 267-269-6432 or emailing


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 25  to January 1 from 10 to 4 p.m., along with weekend nightly tour hours.

Visit for more information.

Chestnut Hill Holiday Parade – TBA

Convenient Shopping Hours:

‘Tis the season for one-of-a-kind finds and specials. Most Chestnut Hill shops are open until 7:00pm or later on Wednesdays through Saturdays during the holiday season for your shopping convenience.  Visit to browse our full array of retail boutiques and restaurants to plan your visit.

Seasonal Pop-ups: Chestnut Hill will have numerous additions to our shopping district in the form of seasonal pop ups along the Avenue.  Stay tuned to our social media for news and updates on what’s new for the holiday season on the Hill

Gift Cards:

For plenty of options when time is short, give the gift of the Chestnut Hill Gift Certificate.  Redeemable at virtually all of Chestnut Hill’s fine shops and restaurants (except Staples and CVS), these convenient gift certificates can be purchased in person at 8514 Germantown Avenue or online at


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 from November 16th through Christmas

Please email any questions to

Thanks to our wonderful holiday sponsors! 

Community Sponsors:

Gold Sponsor:

Silver Sponsors:

Bronze Sponsor: