photo by Daryl Moran for Chestnut Hill Business District
Chestnut Hill comes alive during Holidays on the Hill, a celebration launching November 16 and running through December 25. With festive activities, seasonal cheer, and a warm community spirit, these holiday events promise to make the most wonderful time of the year even more magical. This year, families can visit Morris Arboretum & Gardens to enjoy the ever popular Holiday Garden Railway, indulge in hot chocolate, cookies, and other goodies during the Woodmere Art Museum’s annual Circle of Trees celebration, or explore a selection of Chestnut Hill’s most stunning homes decked out in festive decorations during the Chestnut Hill Community Association’s Holiday House Tour.
For those looking for the perfect holiday gift, Chestnut Hill’s famous Stag & Doe Nights return, giving shoppers a magical experience as they stroll the charming cobblestone streets of Germantown Avenue visiting local businesses offering one-of-a-kind, handcrafted items. To encourage shopping in Chestnut Hill, visitors can take advantage of free parking promotions starting November 29. The Chestnut Hill Parking Foundation will offer free parking in its six public lots every Wednesday, all day and night, through Christmas. Visitors can find a map and more details about the six parking lots here. From the excitement of seasonal pop-ups along the avenue and everything in between, Chestnut Hill’s vibrant holiday traditions make it the perfect seasonal destination.
Holidays on the Hill Schedule of Events
● Circle of Trees – November 23: Families and neighbors are invited to gather at the Woodmere Art Museum (9201 Germantown Avenue) on November 23 for the annual Circle of Trees celebration. The free festivities begin at 5:30 p.m., where guests can indulge in hot chocolate, cider, and cookies while enjoying festive music and goodie bags for the kids. Santa himself will make a grand entrance, arriving on a charming antique fire truck, adding extra magic to the evening. Together, visitors can count down to the lighting of the Art Museum and surrounding trees. Families are encouraged to bring a new unwrapped toy or a new, gently used book to donate to a school-aged child.
● Holiday Garden Railway – November 23 through December 30: The Holiday Garden Railway at Morris Arboretum & Gardens (100 E. Northwestern Avenue) returns November 23 and continues daily from 10 a.m. to 4 p.m. through December 30. Visitors can view the enchanting rail cars and intricately decorated villages, which span over a third of a mile track surrounded by a festive wonderland of lights and sounds. Holiday Garden Railway is a marvelous experience for visitors of all ages.
● Small Business Saturday – November 30: Shop Chestnut Hill’s trendy and one-of-a-kind boutiques during Small Business Saturday and #KeepItOnTheHill. Check off gifts from your holiday wish list and support local retailers and restaurants throughout the day. From 1 to 3 p.m., visitors can meet Santa as he strolls up and down Germantown Avenue and enjoy classic holiday tunes sung by Christmas carolers dressed in Victorian attire, evoking the charm of a Dickens novel!
● Stag & Doe Nights – December 4, 11, 18: Chestnut Hill’s beloved annual Stag & Doe Nights return Wednesday, December 4, during Holidays on the Hill from 5 to 9 p.m. Each night features unique entertainment, extended store hours, holiday specials, and complimentary refreshments and treats at many stores. Every Stag & Doe night, most stores extend their hours until 9 p.m., allowing shoppers to enjoy a festive evening. From 6:30 to 8:30 p.m., visitors can catch a glimpse of Santa strolling down the Avenue, greeting families and spreading holiday cheer while the joyful sounds of a brass quartet fill the air.
● Arts & Eats First Friday – December 6: Guests can stroll the cobblestone streets of Germantown Avenue during Chestnut Hill’s monthly Arts & Eats First Friday event on December 6. From 5 to 9 p.m., families can immerse themselves in the arts and indulge in delicious flavors, all while being surrounded by enchanting holiday lights and decorations that bring a Hallmark-like charm to the neighborhood. Children can enjoy a special visit from Santa and delight in the festive melodies of a brass quartet during First Friday, between 6:30 and 8:30 p.m.
● Chestnut Hill Community Association Annual Holiday Parade – December 7: The Chestnut Hill Community Association Annual Holiday Parade takes place on December 7 at 9 a.m. at Chestnut Hill and Germantown Avenues. It finishes at 10 a.m. at Market at the Fareway (8221 Germantown Avenue). Entertainment includes the Phillie Phanatic, fire engines, marching bands, choirs, antique cars, horses, and participating local schools.
● Chestnut Hill Community Association’s Holiday House Tour – December 14: From 10 a.m. to 4 p.m. explore a curated selection of Chestnut Hill’s most stunning homes, each adorned with unique and festive decorations that capture the spirit of the season during the Chestnut Hill Community Association’s Holiday House Tour. Enjoy live holiday music, treats, and special discounts at Chestnut Hill restaurants and retailers. Attendees have the option of riding the event trolley from stop to stop or visiting at their own pace during the self-guided tour.
Philadelphia RowHome Magazine's Blog 