PHILADELPHIA, PA — Twinkling storefronts, Victorian carolers, visits from Santa Claus, and a holiday tradition more than 50 years old will transform Chestnut Hill into a festive destination as the neighborhood welcomes the return of Holidays on the Hill.
The six-week celebration begins Wednesday, Nov. 18, and continues through Dec. 31, bringing holiday shopping, live entertainment, family activities and seasonal attractions to Germantown Avenue and surrounding destinations.
Organized by the Chestnut Hill Business District, the celebration encourages visitors to explore locally owned boutiques, specialty shops, restaurants, and cultural attractions while enjoying traditions that have become part of the neighborhood’s holiday identity.
This year’s festivities include the Circle of Trees celebration, Small Business Saturday, the annual Holiday Parade, a tour of decorated homes, and the return of Stag & Doe, Chestnut Hill’s longstanding Wednesday evening shopping tradition.
Stag & Doe Keeps a 50-Year Holiday Tradition Alive
One of the celebration’s most recognizable traditions is Stag & Doe, a holiday shopping event that began more than five decades ago as a way for Center City workers to visit Chestnut Hill businesses after their workday.
Today, the tradition continues with extended shopping hours, seasonal specials, live entertainment, and visits from Santa Claus.
This year’s Stag & Doe evenings are scheduled for Dec. 2, 9, 16 and 23.
Shoppers can stroll Germantown Avenue while a brass quartet performs from 6:30 to 8:30 p.m., browse independently owned stores, and enjoy complimentary refreshments offered by participating businesses.
Santa will also make appearances along the Avenue, greeting families and adding to the festive atmosphere.
Many Chestnut Hill shops will remain open until 7 p.m. or later Wednesdays through Saturdays during the holiday season, giving visitors additional opportunities to shop and dine.
To make holiday visits easier, the Chestnut Hill Parking Foundation will provide free parking all day and evening on Wednesdays from Nov. 25 through Christmas in six public parking lots.
Holiday Festivities Begin November 18
Holidays on the Hill opens Wednesday, Nov. 18, with Silent Night, an evening of shopping, dining, and live holiday music along Germantown Avenue.
The celebration continues Saturday, Nov. 21, with Circle of Trees at Woodmere Art Museum.
The family-friendly event will feature music, refreshments, and the lighting of community Christmas trees.
Children can watch Santa Claus arrive aboard an antique fire truck, share their holiday wishes, and explore Woodmere’s Straw Maze while waiting for the tree-lighting celebration.
Festive music from the Philadelphia Mummers will add to the evening’s entertainment.
The following Saturday, Nov. 28, Chestnut Hill will participate in Small Business Saturday, encouraging visitors to support neighborhood retailers while discovering gifts from independent shops.
Victorian-style carolers and Santa Claus will stroll Germantown Avenue from noon to 3 p.m., providing entertainment for families exploring the shopping district.
Holiday Parade Brings Santa to Germantown Avenue
Marching bands, antique cars, community organizations, and Santa Claus will take part in Chestnut Hill’s Holiday Parade on Saturday, Dec. 5.
The annual procession will bring music and seasonal entertainment to Germantown Avenue, giving residents and visitors another opportunity to celebrate together.
On Saturday, Dec. 12, the Holiday House Tour will invite guests inside a selection of Chestnut Hill’s private residences decorated for the season.
The tour offers an opportunity to experience the neighborhood’s distinctive architecture and holiday decorating traditions.
Additional holiday shopping activities will feature live music, seasonal refreshments, and extended business hours throughout the celebration.
Miniature Trains Return to Morris Arboretum
Another seasonal favorite returns when Morris Arboretum & Gardens presents its Holiday Garden Railway from Nov. 21 through Dec. 30.
The outdoor display features a quarter-mile railway with 15 intricate tracks, miniature towns, train cars, and figures constructed using natural materials.
Located at 100 E. Northwestern Avenue, the attraction offers families an opportunity to explore detailed miniature landscapes as trains travel through the seasonal setting.
Visitors can also discover handmade gifts at the Woodmere Art Museum Store, which features work by local artists.
Together, the railway, museum activities, and neighborhood shopping events provide several ways for families to experience Chestnut Hill throughout the holiday season.
Supporting Chestnut Hill’s Independent Businesses
A central part of Holidays on the Hill is the opportunity to support the neighborhood’s independently owned businesses.
Chestnut Hill’s “Keep it on the Hill” initiative encourages residents and visitors to shop locally, particularly during the busy holiday season.
The neighborhood’s boutiques, specialty retailers, galleries and restaurants will offer a range of gifts, seasonal merchandise and dining opportunities.
Decorated storefronts, strolling performers and complimentary refreshments at participating businesses will help create a festive atmosphere along Germantown Avenue.
For visitors searching for unusual gifts or hoping to spend an afternoon exploring a walkable shopping district, the celebration offers an alternative to traditional shopping centers.
Event Details
- What: Holidays on the Hill, a six-week holiday celebration featuring shopping, live entertainment, Santa visits, community traditions, a parade, decorated homes, and seasonal attractions.
- When: Wednesday, Nov. 18, through Thursday, Dec. 31, 2026. Individual event dates and times vary. Most participating shops offer extended holiday hours until 7 p.m. or later Wednesdays through Saturdays.
- Where: Germantown Avenue and surrounding locations in Chestnut Hill, Philadelphia, PA 19118. Activities also take place at Woodmere Art Museum and Morris Arboretum & Gardens, 100 E. Northwestern Avenue, Philadelphia, PA 19118.
- Cost/Tickets: Holidays on the Hill is free to attend. Shopping, dining, and certain separately operated attractions or tours may involve additional costs.
- More Info: Complete event information and updates are available at https://chestnuthillpa.com/holidays-on-the-hill/.
2026 Holiday Events Calendar
- Wednesday, Nov. 18 — Silent Night: An evening of shopping, dining, and live holiday music along Germantown Avenue. Specific hours were not provided.
- Saturday, Nov. 21 — Circle of Trees: Community tree lighting at Woodmere Art Museum, featuring Santa arriving by antique fire truck, festive music, and family activities. Specific hours were not provided.
- Nov. 21–Dec. 30 — Holiday Garden Railway: Seasonal miniature railway display at Morris Arboretum & Gardens, 100 E. Northwestern Avenue. Daily operating hours vary.
- Saturday, Nov. 28 — Small Business Saturday: Holiday shopping at local businesses, with Victorian carolers and Santa visits from noon to 3 p.m.
- Wednesdays, Dec. 2, 9, 16 and 23 — Stag & Doe: Extended shopping hours, holiday specials, Santa appearances and brass quartet performances from 6:30 to 8:30 p.m.
- Saturday, Dec. 5 — Holiday Parade: Marching bands, antique cars, community groups and Santa Claus along Germantown Avenue. The parade’s starting time was not provided.
- Saturday, Dec. 12 — Holiday House Tour: Visits to decorated private residences in Chestnut Hill. Tour hours and ticket prices were not provided.
From the sounds of carolers along Germantown Avenue to the sight of miniature trains winding through holiday landscapes, Holidays on the Hill offers a variety of ways to celebrate the season.
Families can enjoy visits with Santa, shoppers can discover gifts from neighborhood businesses, and longtime residents can revisit traditions that have connected generations of Chestnut Hill visitors.
With festivities continuing through New Year’s Eve, the neighborhood’s holiday celebration provides opportunities to enjoy local businesses, seasonal entertainment, and community gatherings throughout November and December.
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