During Holidays on the Hill, visitors can immerse themselves in the season’s spirit by strolling through one of Philadelphia’s most historic villages! Guests can enjoy the holiday cheer of Chestnut Hill with a brass quartet, view an outdoor model train display at Morris Arboretum and take advantage of late-night shopping hours on Wednesdays. Refreshments are served at many local businesses to add charm to the season, and guests can have their picture taken with our beloved Santa!

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 has vibrant holiday traditions. 

Santa will be at MARKET at the Fareway Saturdays from December 12-2 p.m.

2023 Festival Attractions Include:

November 18 – Circle of Trees A perennial favorite of local families and children, Chestnut Hill’s kick-off to the holiday season will happen this year on November 18th, 5:30-7 p.m with Santa’s firetruck arriving so he can hear children’s wishes.  Woodmere’s Straw Maze is open while we wait for Santa.  The Highway Patrol motorcycles will lead Santa in so he can turn on Woodmere’s holiday lights. Parking available at the museum lot with additional parking on the Sugarloaf Campus parking lots.  

November 25 – Small Business Saturday 

Shopping small is a way of life in Chestnut Hill.  Our motto of “Keep it on the Hill” is a commitment among Chestnut Hill residents to keep our dollars as local as possible and as Philadelphia-made as we can.  Check off everything on your list by supporting independent businesses in a charming, walkable urban village. Shoppers are sure to find the perfect gift for loved ones this season in our unique boutiques and specialty shops.  Join classic Philadelphia mummers from 1-3 p.m. and Santa Claus from 12-3 p.m., to experience the most magical and nostalgic shopping experience in the Philadelphia region!  

November 29 & December 6, 13, & 20 – Stag & Doe Nights

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.

December 2 – The Chestnut Hill Community Association Annual Holiday Parade  (Rain Date December 17)

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 list.at Woodmere’s Museum Store also offers online 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 25  to December 30 from 10 to 4 p.m., along with nightly tours on select weekend dates.

Visit Morris Arboretum for more information.

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 https://chestnuthillpa.com/business/ 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 this year 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 10 E. Springfield Avenue or online at https://chestnuthillpa.com/shop/chestnut-hill-gift-certificate/.


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 29th through Christmas.

Please email any questions to inquiry@chestnuthillpa.com