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

Saturday, November 21

Due to new City of Philadelphia regulations we will have to cancel the Santa Drive-by part of the Circle of Trees event on Saturday, November 21. You can still see Santa virtually and listen to him read a beautiful edition of Twas the Night Before Christmas and then help him count down to the lighting of Woodmere Art Museum and their Christmas tree. Register for the Zoom link at: Register HERE for details

Small Business Saturday

Saturday, November 28

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

Wednesdays, December 2, 9, 16, 23, 11:00am-9:00pm.

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 and continues through January 3. 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.

New in 2020!

The Gift That Keeps On Giving: Chestnut Hill Holiday Gift Certificate Promotion.

This holiday season, give the gift of local shopping and earn chances to win additional prizes with every purchase of a Chestnut Hill Gift Certificate.  Available in convenient $25 and $50 denominations, the certificates are the perfect gift for anyone who enjoys distinctive boutique shopping, delicious culinary experiences, luxurious personal services, and the charming backdrop of Philadelphia’s urban village.  Chestnut Hill Gift Certificates are a socially-responsible gift that promises valuable support to the neighborhood’s 225 small businesses.  Plus, for every $25 you spend, you will be entered into a post-holiday drawing to win additional gift certificates, food from local restaurants, and free gifts! Prizes include:

  • Chestnut Grill -50.00 gift card
  • Greene Street  -$25 gift card
  • Night Kitchen Bakery -8″ birthday cake. (Value $38.50- serves 10 to 12)
  • Chestnut Hill Sports -$20 gift card
  • McNally’s Tavern -50.00 gift card
  • Tavern on the Hill -25.00 Gift Card
  • El Quetzal -20% off one full priced item
  • Chestnut Hill Gift Cards: Two $25 Gift Cards

Order your gift cards in person at the Chestnut Hill Welcome Center at 8514 Germantown Avenue, by calling 215-247-6696, or purchase online at

Live Stream Holiday Shopping Previews

December 1, 8, 15, and 22

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.  The following retailers have committed to being open until 7pm or later Wednesdays through Saturdays every week between Thanksgiving and Christmas.  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 (December 2, 9, 16, 23) from 5:00-9:00pm.

2020 Holiday Entertainment Schedule

  • Strolling Santa Claus*: 
    • Small Business Saturday, November 28: 11 a.m.-2 p.m.
    • Wednesday, December 2: 6-9 p.m.
    • Saturday, December 19: 2:00-5:00 p.m.
    • Wednesday, December 23: 11 a.m.- 2 p.m

*Due to the COVID-19 pandemic, Santa Claus is unable to offer seated meetings with children.  However, he will be strolling the Avenue wearing his new mask that Mrs. Claus sewed for him, greeting shoppers and families during the times and dates given above.  Children are welcome to speak with Santa from 6 ft away with masks in place too!

  • Mummers Trio:
    • Small Business Saturday, November 28: 1-3 p.m.
  • Brass Quartet:
    • Wednesdays, December 2, 9,and 23: 6:30-8:30 p.m.
    • Saturday, December 19, 2020, 12:30-2:30pm
  • Horse-Drawn Carriage Rides: Carriages depart from 8532 Germantown Avenue (corner of Germantown and Evergreen Avenues).  Rides are free, courtesy of the George Woodward Company, and are available on a first-come, first-served basis.  The last ride departs 20 minutes prior to the posted end time.  Rides will be available at the following dates/times:
    • Small Business Saturday (Saturday, November 28, 2020), 3:00-6:00pm
    • Saturday, December 19, 2020, 2:00-5:00pm
    • Chestnut Hill Stag and Doe #4 (Wednesday, December 23, 2020), 6:00-9:00pm

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 through the end of 2020, beginning 11/28.

Thank You To Our Wonderful Holiday Sponsors

2020 Community Sponsors:

Presenting Sponsor

Other Sponsors