Chestnut Hill Business District
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Holidays on the Hill

Holidays on the hill
Immerse yourself in the holiday spirit in Chestnut Hill, one of Philadelphia’s most beautifully tree-aligned neighborhoods! From Small Business Saturday to the legendary Stag & Doe Nights every Wednesday between Thanksgiving and Christmas, Chestnut Hill offers holiday traditions that bring the past and present together.
Chestnut Hill is the perfect place to discover unique, one-of-a-kind gifts from local boutiques and specialty shops.

Festive Entertainment

Enjoy the sounds of a brass quartet, live carolers strolling the Avenue, and an outdoor model train display at Morris Arboretum.

Meet Santa

Snap a photo with our beloved Santa and create lasting memories!

Late-Night Shopping

Shop local treasures on Wednesdays with extended store hours and holiday specials.

Seasonal Treats

Savor complimentary refreshments at many local businesses while you explore.

2025 Festival Attractions

Circle of Trees

A family favorite to start the Holiday season! Watch Santa arrive on a firetruck to hear children's wishes, explore Woodmere's Straw Maze while waiting for Santa to light up the holiday display, and enjoy festive tunes from the Philadelphia Mummers as we officially kick off Holidays on the Hill.

Shop Small Business Saturday

Support local businesses while enjoying the charm of our walkable urban village. With our motto, "Keep it on the Hill," we're proud to make shopping small a way of life. Explore independent boutiques and specialty shops to check off your holiday list.
Enjoy carolers in Victorian dress and visits from Santa Claus roaming the Avenue from 12–3 PM.

Stag & Doe Nights

Join us every Wednesday from Thanksgiving to Christmas for this cherished holiday tradition featuring extended store hours & specials, festive entertainment with a brass quartet from 6:30–8:30 PM, Santa strolling the Avenue greeting families, and seasonal treats at many stores.

Arts & Eats: Holiday Edition

Extended store hours & specials, live music with a brass quartet from 6:00–8:00 PM, Santa sightings along the Avenue, and complimentary refreshments at many local shops.

Special Attractions

Woodmere Art Museum
Shop one-of-a-kind gifts created by talented local artists at Woodmere's Museum Store. Visit in person or shop online for everyone on your list.

Garden Railway at Morris Arboretum
Don't miss the beloved Holiday Garden Railway returning Thanksgiving weekend! A dazzling quarter-mile train display with 15 intricate rails, miniature towns, train cars, and figurines, all crafted from natural materials. Located at 100 E. Northwestern Avenue.

Holiday Shopping Hours

Most shops stay open until 7:00 PM or later on Wednesdays through Saturdays during the holiday season.

Free Parking

Every Wednesday from November 29 through Christmas, enjoy free parking all day and night in six public lots courtesy of the Chestnut Hill Parking Foundation.