A stone house with ivory sash windows and a slate roof overlooks a gently sloping autumn lawn and curved flagstone approach.

Chestnut Hill's 2026 Holiday Season: The Saturdays Where Everything Lands at Once

On Saturday, December 12, the day starts at St. Joseph's Hall on the Chestnut Hill College campus, 9601 Germantown Avenue. That's where Holiday House Tour guests pick up a map, a wristband and shoe booties before heading out to the decorated homes. The tour wraps up at 4 p.m. Half an hour later, Morris Arboretum & Gardens opens its gates for an evening of HGR: Nighttime Express, with laser lights in the trees above the Holiday Garden Railway.

The Chestnut Hill Business District lists Holidays on the Hill as running from November 18 to December 31, 2026. But the major community events this year fall on three Saturdays, and each one shares its date with the railway at Morris. The house tour and the evening railway visits both need tickets bought ahead of time, and the railway evening tickets go on sale in the first half of November.

Every Date Moved Up by One Day

Compare the 2026 schedule with last year's and you'll see a pattern. In November 2025, MyChesCo reported last season's dates: Circle of Trees on November 22, Stag & Doe Nights on December 3, 10 and 17, the Holiday Parade on December 6, and the Holiday House Tour on December 13. This year, every one of those events falls one calendar date earlier.

Event 2025 2026 Day of week
Circle of Trees at Woodmere November 22 November 21 Saturday
Holiday Garden Railway daytime opening November 22 November 21, per Morris's schedule Saturday
Stag & Doe Nights December 3, 10, 17 December 2, 9, 16 Wednesday
Holiday Parade December 6 December 5 Saturday
Holiday House Tour December 13 December 12 Saturday

The events are tied to days of the week, not to calendar dates. Stag & Doe is a Wednesday tradition. The parade, the house tour and Circle of Trees are Saturday events. Morris's evening railway visits, called Nighttime Express, run mostly on weekends. When three community traditions and a ticketed attraction all stick to the same weekdays, they end up on the same few days every year. In 2026 those days are November 21, December 5 and December 12.

November 21: Two Openings, One Evening

The season unofficially opens on a Saturday in two parts. Morris's Holiday Garden Railway page lists daytime viewing from November 21 to December 30, included with general admission. The FAQ on the same page gives daily hours of 10 a.m. to 4 p.m. starting November 22, so it's worth checking with Morris before planning around opening day. Daytime visits no longer need an advance ticket. The display is outdoors: a third of a mile of track with loops and tunnels set among plants and lights. The trains don't run in heavy rain, snow or ice.

At 5:30 p.m. that same evening, the Circle of Trees Celebration begins at Woodmere. The Chestnut Hill Community Association presents it with the Business District and the museum. There's hot chocolate, cookies, music and goodie bags for kids. Santa arrives on a fire truck, and the crowd counts down to the lighting of the museum and the Christmas trees. The event is free. The CHCA asks guests to bring a new, unwrapped toy or a new book to donate to a school-aged child.

If the railway does open on the 21st, its daytime hours end at 4 p.m. and Circle of Trees starts 90 minutes later, so the two don't overlap. If Morris confirms the FAQ's November 22 date instead, the railway becomes the Sunday half of the opening weekend.

December 5: Parade Morning, Railway Night

The CHCA Holiday Parade runs from 9 a.m. to noon on Saturday, December 5. According to MyChesCo, last year's parade included marching bands, antique vehicles, fire engines, horses, Santa and the Phillie Phanatic. That's last year's lineup, not a confirmed 2026 roster.

That evening is also one of the first four Nighttime Express dates at Morris. The general schedule starts with two weekends of Saturday and Sunday visits only: November 28 and 29, then December 5 and 6. General weeknight sessions don't begin until Thursday, December 10. The only weeknight evenings before then are December 3 and 4, which are set aside for Premier members. If a household wants an evening railway visit in the first half of December, the parade weekend is one of only two weekends to choose from.

Sunday the 6th has its own family option. Woodmere lists a family art and storytelling program on December 6.

December 12: The House Tour Hands Off to the Railway

The CHCA calls the Holiday House Tour "Philadelphia's longest running holiday tour," and it's a major fundraiser for the association. It runs from 10 a.m. to 4 p.m. on December 12. Recent tours have included a cottage, a stone colonial, a three-story Italianate Victorian, a Second Empire twin and a Norman country house.

Here's how the day works, based on the CHCA's description:

  • Check-in: St. Joseph's Hall, Chestnut Hill College, 9601 Germantown Avenue, where you get your map, wristband and booties.
  • Getting around: The tour is self-guided. You can drive, or ride the event trolley, which stops at each house and along Germantown Avenue.
  • Breaks: The trolley also stops at a warming station with treats and warm drinks, hosted by Home Works.
  • Shopping: The CHCA says many restaurants and shops will offer discounts to tour attendees.
  • Weather: The tour runs rain or shine.

Tickets are on sale now: $45 for CHCA members, $50 for non-members, and $400 for a group of 10, which works out to buying nine tickets and getting the tenth free. All proceeds go to the Chestnut Hill Community Association.

The tour ends at 4 p.m., and Nighttime Express begins at 4:30 the same evening. December 12 also falls in the first of the season's two four-night runs, Thursday, December 10 through Sunday, December 13. The second runs December 17 through 20. The Morris's address is 100 E. Northwestern Avenue, as listed in the Chestnut Hill Local's 2025 holiday guide. Planning a full day like this means you'll need a house tour ticket for the morning and a timed railway ticket for the evening.

The Weeknights Between the Saturdays

The Saturdays draw the crowds, and Germantown Avenue's own events fill the weeknights. The Business District's December calendar lists Stag & Doe Nights from 6 to 9 p.m. on Wednesdays, December 2, 9 and 16. One confirmed 2026 entertainment listing so far is singer Reny Sawitri at From Bali to Us on December 2, from 7 to 9 p.m.

The same calendar lists Arts & Eats from 5 to 8 p.m. on Friday, December 4, and a Liwetan dinner at From Bali to Us from 7 to 8 p.m. that evening. That makes Friday the 4th a lead-in to the parade weekend.

Last year's Stag & Doe Nights came with late store hours, a brass quartet, a Santa stroll from 6:30 to 8:30 p.m., and free Wednesday parking in six public lots, according to Business District pages published in November 2025. The District hasn't yet posted whether those extras return for 2026.

The Saturday after Thanksgiving is less settled. In 2025, the Chestnut Hill Local described a Small Business Saturday program on November 29 with Courtney's Carolers, Santa and business deals. As of late October, the only November 28 listing on the District's November calendar is the regular Chestnut Hill Farmers Market, 9 a.m. to noon at Germantown Avenue and Mermaid Lane. That evening is also the first night of Nighttime Express.

What to Book, in Order

Nighttime Express has 12 evenings this year, each from 4:30 to 8 p.m. Because parking is limited, every ticket comes with a specific arrival time, so the evenings that line up with the big Saturdays are the ones to book first. Here's the order:

  1. Morris members: Member tickets for Nighttime Express went on sale November 2: $17 per adult and $10 per youth ages 3 to 17. Premier members can also attend one free member night on December 3 or 4, from 4:30 to 8 p.m.
  2. Everyone else, starting Monday, November 9: General tickets go on sale at $22 per adult and $12 per youth. Children 2 and under are free. A daytime admission ticket doesn't include the evening, and you can't stay from a day visit into Nighttime Express.
  3. House Tour tickets for December 12: On sale now through the CHCA's ticket page, at the prices listed above.
  4. No ticket listed: Circle of Trees on November 21 is free, per the CHCA; bring a new, unwrapped toy or a new book. The District's listings for the December 5 parade and the Stag & Doe Wednesdays don't mention tickets.

Morris is closed December 24, 25 and 31 and January 1. The last daytime railway viewing is December 30, and the last Nighttime Express evening is Sunday, December 20.

At The Sivel Group, we plan around these dates too: the parade Saturday, the house tour and the Wednesday evenings on the Avenue are part of what makes December in Chestnut Hill what it is. If you're thinking about how your own home might look on a future Holiday House Tour, or what a December move around these weekends would involve, we're happy to talk it through. Sell smarter. Buy smarter. Move smarter.

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