Type to search




The Philadelphia community of Chestnut Hill is a charming year-round destination. During the holiday season the town truly shines. The picturesque neighborhood, which is conveniently located near the Main Line, mixes Old World charm with modern amenities. From Thanksgiving through New Year’s, the area is abuzz with activities and events perfect for families, friends and couples.

“During ‘Holidays on the Hill’, Chestnut Hill is aglow as thousands of white lights twinkle in the trees, fresh pines adorn shop windows, carolers sing and brass quartets entertain,” says Martha Sharkey, the executive director of the Chestnut Hill Business District. “This is quite a unique urban village, tucked away in the northwestern corner of Philadelphia along the Wissahickon, where guests will find a convergence of old and new, metropolitan and pastoral.” With its old fashioned stone architecture, the town is something out of a fairytale this time of year, accented by holiday cheer, welcoming residents and friendly business owners.

To celebrate the spirit of the holidays, the town hosts various events throughout the season, starting with the Circle of Trees. A quintessential kick off to the holiday season, Woodmere Art Museum – decked in full holiday regalia, hosts this event on November 19. The St. Thomas Church Choir and Norwood Fontbonne Academy Chorale perform as guests sip hot chocolate and cider. Throughout the season, Woodmere also hosts ‘Twas the Night Before Christmas,” running November 19 through January 8, during which the classic tale of “The Night Before Christmas” is brought to life through artifacts, including antique children’s toys.

“The holidays provide an amazing opportunity to create excitement within our community while giving visitors the chance to experience Chestnut Hill’s charm,” says Sharkey. Chestnut Hill welcomes visitors from near and far, inviting them to explore one of the City’s premier shopping districts, comprised of small businesses, independent retailers, galleries and world-class restaurants – all enhanced with events and programming for the holidays.

Visitors can find an array of boutique shopping, including elegant and chic women’s fashion at Sara Campbell and Style Camp, a range of home décor and furnishings on consignment at Phantastic Phinds, creative cakes and decorating supplies at Ella Vanilla, or amazing rugs and carpets at Woven Legends and Claudia Mills. The Hill Company and Isabella Sparrow are musts for those seeking interior or exterior furnishings.

Beyond shopping, Chestnut Hill has many galleries to peruse, perfect for those seeking unique, one-of-a-kind gifts for the holidays. The community is host to a plethora of independent art galleries, thriving artists, museums, and cultural events. A staple along Germantown Avenue, Gravers Lane Gallery offers a range of works in different mediums, including fibers, jewelry and glass, while the Philadelphia Print Shop offers antique maps, prints and rare books, making them the perfect stop for the antiquarian or bibliophile.

Many of those shops offer special events and deals for Small Business Saturday, taking place November 26 this year. “Our shops are committed to supporting each other while maintaining the inherent charm of this historic district,” adds Sharkey, and this time of year is no exception.  

For the night owls, Stag & Doe Nights are the perfect time to get in some extra shopping. Stores in Chestnut Hill stay open late, from 6 to 9 p.m., on Wednesdays Nights throughout the holidays (Nov. 30 and Dec. 7, 14, 21). This long-standing tradition is even merrier with all the shops decorated for the season, Santa strolling the Avenue, and a brass quartet playing around town. Plus, visitors can enjoy wine and cheese or hot chocolate throughout the night.

Other holiday events include the Holiday House Tour on December 3, where visitors will get a peek inside lavishly decorated homes. The Annual Community Holiday Parade and Sugarplum Saturday will take place on December 10.  Morris Arboretum also hosts its annual Holiday Garden Railway and Friday Night Lights from November 25 through December 31, in which model trains rush across a quarter mile of track, surrounded by twinkling lights, perfect for families.

“Chestnut Hill is the ideal holiday destination. Whether it’s a shopping excursion or relaxing respite, we truly offer something for everyone,” adds Sharkey. A green community paired with the cheerful and elegant decorations that abound during the holidays, Chestnut Hill is the perfect place to visit this holiday season.Visitors can cap a day in Chestnut Hill with a delicious meal from a range of cuisines. With more than 25 restaurants, pubs, and eateries throughout Chestnut Hill, guests can enjoy globally inspired options ranging from American cuisine to Asian Fusion, a Parisian bistro or a Mexican-inspired cantina. Those just looking for a quick caffeine fix or a hot beverage can pop into Chestnut Hill Coffee or Roller’s Express-o to warm up in a cozy environment. The Market at the Fareway is another great spot to escape the cold. Visitors can meander among the many vendors or sip outside by the fire pit.

For more information on Chestnut Hill, its events, shops and more, visit www.chestnuthillpa.com.

Summer flash sale!

Save 50% today on a subscription to Main Line Today

Limited time offer. New subscribers only.

Summer flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.