PHILADELPHIA, PA — Chestnut Hill is set to transform once again into a storybook winter village as its annual Holidays on the Hill celebration kicks off November 22, launching more than a month of festive events, shopping nights, and family traditions that stretch through Christmas Day.
The seasonal showcase turns the historic Northwest Philadelphia neighborhood into a bustling holiday destination, complete with twinkling lights, house tours, musical performances, and cherished community gatherings. Organizers say this year’s lineup blends time-honored favorites with special moments designed to bring residents and visitors together.
The celebration begins November 22 with Circle of Trees, a beloved community tradition at the Woodmere Art Museum featuring hot cocoa, cookies, live music, goodie bags for children, and a dramatic arrival by Santa aboard an antique fire truck. Guests are encouraged to donate new or gently used books for local students.
That same day marks the opening of the Holiday Garden Railway at Morris Arboretum & Gardens, where model railcars wind through a glowing landscape of lights and evergreens. Open daily through December 30, it remains one of the region’s most popular holiday attractions for families of all ages.
Shoppers will find plenty to explore as Chestnut Hill’s boutiques and small businesses roll out seasonal specials. Small Business Saturday on November 29 encourages visitors to “Keep It on the Hill,” while the neighborhood’s famous Stag & Doe Nights return December 3, 10, and 17. During these festive Wednesdays, Germantown Avenue comes alive with extended store hours, refreshments, roaming entertainment, and free parking in all six Chestnut Hill Parking Foundation lots.
On December 6, the Chestnut Hill Community Association Holiday Parade steps off at 9 a.m., featuring marching bands, antique vehicles, fire engines, horses, and appearances by Santa and even the Phillie Phanatic. The celebration continues December 13 with the district’s annual Holiday House Tour, inviting guests to explore elegantly decorated homes by trolley or on foot, accompanied by live music and exclusive local shopping perks.
Holidays on the Hill is organized by the Chestnut Hill Business District, which represents more than 200 local shops, restaurants, and organizations. The district says the monthlong celebration offers something for everyone — from treasured traditions to new ways to experience the neighborhood’s seasonal charm.
Festivities run through December 25.
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