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 Garden District. 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 socially-distanced visits from Santa! This year, the Chestnut Hill Business District has implemented new COVID-19 safety guidelines, reimagining Holidays on the Hill to create various safe and socially distant ways to celebrate the holidays, virtually or in-person. Chestnut Hill’s oldest tradition, Stag & Doe, is expanding to an all-day event, with staggered entertainment, to provide for a comfortable, safe, and socially distant shopping experience.

Don’t Miss these Beloved Holiday Traditions:

Circle of Trees

Small Business Saturday

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 the mummers and experience the most magical shopping experience in the Philadelphia region!

Stag & Doe Nights

While many aspects of the season have been turned upside down, Chestnut Hill is keeping traditions intact, safely and socially distanced. The beloved annual Stag & Doe Nights will take place every Wednesday in December and feature extended store hours, holiday specials, and horse-drawn carriage rides. You may even catch a glimpse of Santa strutting down the Avenue as the sounds of a cheerful brass quartet fill the air. 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 track, surrounded by natural materials, multiple train cars, towns, and miniature figurines.  Visit for more information.

Live Stream Holiday Shopping Previews

Tune into the Chestnut Hill Facebook page ( every Tuesday in December leading up to Christmas to see featured items, seasonal specials, and great holiday gift ideas from some of Chestnut Hill’s most popular shops.  More details and schedule of participating shops coming soon!

VIP & Private Shopping Experiences

This year, you can stay safe and enjoy a personalized holiday shopping experience at some of Chestnut Hill’s finest boutiques.  Click on the following retailers’ pages and contact them to schedule a private shopping time when you can view inventory, make purchases, and enjoy the individualized attention of sales associates without distraction or contact with other shoppers.  There’s simply no better way to shop in Chestnut Hill.  Available at:

7pm or Later, Guaranteed! | Standardized Evening Hours for Convenient Shopping

There’s no need to worry about your favorite shops being closed when you visit Chestnut Hill this holiday season.    Visit retailers’ pages by clicking on their names to check their individual hours.

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 safely conducted outdoors at 8527 Germantown Avenue, near the intersection with E. Evergreen Avenue.   The Stateside stand will be open on Stag and Does  from 5:00-9:00pm.

Free Parking Promotions

For the benefit of our customers, we are pleased to share two Free Parking promotions this holiday shopping season:

  • Wednesdays In Our CHPF Lots: In celebration of Stag and Does, the Chestnut Hill Parking Foundation is offering free parking in its six public lots all day and night every Wednesday between Thanksgiving and Christmas.
  • Saturdays On The Streets: The Philadelphia Parking Authority is offering citywide free metered street parking from 11:00am to 6:00pm every Saturday.

Thank You To Our Wonderful Holiday Sponsors

2021 Community Sponsors:

Presenting Sponsor

Other Sponsors