Chestnut Hill's holiday season starts this Saturday at Woodmere and peaks on the first Saturday of December with the parade. The part that comes back every week happens on Wednesdays. From the day before Thanksgiving through the week of Christmas, Wednesday is the one day the Hill's six public lots are free all day and all night. In December, Wednesday is also when shops on Germantown Avenue stay open into the evening while a brass quartet plays and Santa walks the sidewalk.
The Chestnut Hill Business District runs Holidays on the Hill from November 18 through December 31, 2026, so the season is already underway as you read this. Most of the calendar is single dates you circle once. The Wednesdays are the ones that repeat.
This Saturday, Both Ends of the Hill Light Up
The Hill marks the start of the season on Saturday, November 21, at Woodmere Art Museum, 9201 Germantown Avenue. Circle of Trees runs from 5:30 to 7:30 p.m. It includes a countdown to lighting Woodmere and the trees around it, Santa arriving on an antique fire truck, music, hot chocolate and cookies, goodie bags for kids, and a pop-up shop in the gallery. Admission is free. Woodmere asks guests to bring a new, unwrapped toy or book for children in need, and the event is presented with Norwood-Fontbonne Academy, the Chestnut Hill Business Association, and the Chestnut Hill Community Association. The Chestnut Hill Local's 2026 holiday calendar also lists Mummers music and says Santa will greet children on the museum porch to hear their holiday wishes.
If you're at Woodmere earlier in the day, the Straw Maze is open Saturdays and Sundays from 10 a.m. to 5 p.m. through the end of November. Arc of Promise, the museum's America 250 exhibition on how Philadelphia artists have pictured "America," stays up through January 10.
At the other end of the Hill, the Holiday Garden Railway at Morris Arboretum & Gardens opens for daytime viewing the same weekend. It runs daily from 10 a.m. to 4 p.m. through December 30, and admission to the trains comes with general admission. The Local describes it as one of the largest outdoor model train displays in the country, with 15 lines on a third-mile track at 100 E. Northwestern Avenue. Morris is closed Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve, and New Year's Day. The trains also don't run in heavy rain, snow, or ice.
Both kickoffs are on a Saturday. After that, the Avenue's schedule settles into a weekly pattern.
Wednesday Is the Night the Avenue Is Planned Around
According to the Business District's Holidays on the Hill page, every Wednesday from November 25 through Christmas brings free parking all day and night in six public lots, courtesy of the Chestnut Hill Parking Foundation. The same page says most shops stay open until 7 p.m. or later Wednesday through Saturday during the season. Wednesday is the earliest of those late nights, and it's the only one with free parking.
The first free Wednesday is November 25, the day before Thanksgiving. That's the day for the last grocery run or a pie pickup, with no meter to feed. The four Stag & Doe nights then fill every Wednesday in December before Christmas.
| Wednesday | Parking | On the Avenue |
|---|---|---|
| November 25 | Free in all six lots, all day and night | Day before Thanksgiving |
| December 2 | Free | First Stag & Doe night, 6 to 9 p.m., with a brass quartet and Santa on the Avenue from 6:30 to 8:30 |
| December 9 | Free | Stag & Doe, extended store hours, brass quartet, Santa from 6:30 to 8:30 |
| December 16 | Free | Stag & Doe with sips and snacks at participating shops |
| December 23 | Free | Final Stag & Doe night of the year |
The Local calls Stag & Doe "a Chestnut Hill holiday tradition" and lists free parking in the public lots on each of the four nights. The Local's description of December 23 is the most honest line on the calendar: "This is it – you are out of time!"
The Six Lots, by Color
Free parking only helps if you know where the lots are. The Business District's parking guide lists the six Parking Foundation lots by color:
- Yellow, on East Evergreen Avenue
- Blue, also on East Evergreen Avenue
- Green, on East Highland Avenue
- Orange, at 8300 Germantown Avenue
- Turquoise, on West Highland Avenue
- Purple, at 8600 Germantown Avenue, with the entrance from Hilltop Road and Rex Avenue
The lots cover the middle and upper stretches of the Avenue's shopping blocks. If you start a Stag & Doe night at the Orange lot and finish near Purple, you'll have walked most of the 8300 to 8600 blocks. The two Evergreen lots put you a block off the Avenue, on the same street as Lovat Square, the wine bar at 184 E. Evergreen Avenue. Lovat keeps Thursday-through-Sunday hours, noon to 10 p.m., so it's an option on the late nights after Wednesday.
The Morris Night Trains Never Run on a Wednesday
The Morris's evening schedule fills in around the Wednesday pattern. HGR: Nighttime Express, the after-dark version of the railway with laser lights in the trees and lights along the track, runs from 4:30 to 8 p.m. on these dates:
- Saturday and Sunday, November 28 and 29
- Saturday and Sunday, December 5 and 6
- Thursday through Sunday, December 10 through 13
- Thursday through Sunday, December 17 through 20
None of the dates is a Wednesday. That means you can spend a Wednesday on the Avenue and a Thursday at the trains in the same week without choosing between them. Nighttime Express needs an advance ticket, separate from daytime admission. General tickets went on sale November 9. Prices are $22 for adults and $12 for youth ages 3 to 17, with children 2 and under free. Members pay $17 and $10. A daytime ticket doesn't let you stay into the evening session. Premier members at the Supporter level and above can choose one complimentary members' night, Thursday, December 3 or Friday, December 4, with cookies and hot chocolate on the route.
The First Weekend of December Is the Busiest
Most of the season's one-time events land in a 48-hour stretch, right after the first Stag & Doe Wednesday.
Friday, December 4. Arts & Eats, Chestnut Hill's First Friday, has a holiday edition from 5 to 8 p.m. On a regular First Friday, galleries and retailers stay open until 8 with exhibits, demonstrations, live music, and food and drink specials at restaurants. The December edition adds a brass quartet, Santa, and complimentary refreshments at many shops. At Woodmere, "Substance of Things Hoped For: The Music of Marvin Gaye" starts at 6 p.m. the same night.
Saturday, December 5. The Chestnut Hill Community Association Holiday Parade steps off at 9 a.m. and runs until 10 on Germantown Avenue, from Chestnut Hill Avenue to the Market at the Fareway. It's free, and Santa is in it. The year-round Saturday farmers market sets up at Germantown Avenue and Mermaid Lane, in front of the Mermaid Inn, and runs until noon. Northwestern Stables, at 120 W. Northwestern Avenue, holds its Holiday Horses and Bazaar from 10 a.m. to 3 p.m. Admission is free. Expect handmade gifts and holiday games, plus photos with Santa and his horse, which need pre-registration. Guided horse rides for kids cost extra. That evening, Nighttime Express runs at the Morris.
Sunday, December 6. Woodmere's Sunday Family Art & Storytelling runs from 11 a.m. to noon. It's free, and registration is required.
If you plan to eat on the Avenue that weekend, Blue Warbler at 8001 Germantown Avenue is an all-day cafe and restaurant. The Philadelphia Inquirer reviewed it in September, and owner Fred Mogul told the paper he wanted it to be a communal gathering place.
After the Peak, the Wednesdays Carry On
Once the parade is over, the one-time events thin out. Woodmere has a free lecture on the painter Moe Brooker on Thursday, December 10, at 6 p.m., with registration. The Morris adds Thursday and Friday night-train dates through December 18. The Avenue's own calendar comes down to Stag & Doe on December 9, 16, and 23, each with free parking, extended hours, and Santa between 6:30 and 8:30.
That makes the weeknight plan simple. For a gift you'd rather pick up in person, or a slow loop of the shops with a brass quartet on the street, go on a Wednesday. Park in the Orange or Purple lot, walk the 8300 to 8600 blocks, and catch Santa between 6:30 and 8:30. The last one is December 23.
Those Wednesday evenings are also when the Avenue's storefronts and the houses around them look their best. We spend a lot of time thinking about how that holiday warmth shows up in photos and in person, from window light at dusk to a mantel that looks lived-in rather than staged. If you're thinking about how your Chestnut Hill home will show this winter or next spring, Philly Home Collective is glad to walk through it with you. Work with us.
