The annual Holidays on the Hill schedule has been announced, with a packed schedule of seasonal fun planned for 2025.
The festivities officially kick off in Chestnut Hill on Nov.22, and will continue on in the picturesque neighborhood of the city until Dec. 25. Throughout the multi-week activation, visitors will find festive art exhibits, seasonal shopping opportunities, themed events, food specials and more.
Circle of Trees at Woodmere Art Museum (9201 Germantown Ave.) is the first big free event on the schedule. Taking place Nov. 22 at 5:30 p.m., the evening will feature treats (think cider, hot chocolate and cookies), goodie bags for kids and an appearance from Santa Claus, who will ride in on an antique fire truck.
The main pull of the event, the lighting of the Woodmere Art Museum and surrounding trees, will top off the evening. Families in attendance are just asked to bring a new, unwrapped toy or a new, gently used book to donate to a school-aged child.
Another popular fixture from Holidays on the Hill is housed at Morris Arboretum & Gardens (100 E. Northwestern Ave.) The Holiday Railway will open Nov. 22 and be onsite at the venue until Dec. 30. While there, visitors can peruse through the attraction—which features intricately designed rail cars, villages and more—but with a sparkly holiday twist.
While at the 92-acre horticultural grounds this season, Philadelphians can also explore Morris’ fernery, tree canopy walk, fairy gardens, swan pond, historic structures and pop-up events.
Small Business Saturday (Nov. 29) is another focal point of Chestnut Hill's activation. From noon 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, while also enjoying specials from the area's boutiques.
Stag and Doe nights are also returning in 2025 with multiple dates set for its run. Taking place Dec. 3, 10 and 17 from 5 to 9 p.m., each night features entertainment, extended shopping hours, holiday specials, and complimentary refreshments and treats at some stores.
To encourage shopping throughout Holidays on the Hill, Chestnut Hill is additionally offering a special promotion (starting Nov. 29) to all visitors. The 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 lots online.)
Other Holidays on the Hill events span the Chestnut Hill Community Association Annual Holiday Parade (Dec.6.) and the Community Association's Holiday House Tour (Dec.13.) The former kicks off at 9 a.m., with entertainment spanning the Phillie Phanatic, fire engines, marching bands, choirs, antique cars, horses, and participating local schools.
The latter is another fan favorite, and this year, guests can explore a curated selection of Chestnut Hill homes, each adorned with unique and festive decorations from 10 a.m. to 4 p.m. The occasion also features live holiday music, treats, and special discounts at area 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 as well.
To learn more information, visit chestnuthillpa.com
