Chestnut Hill’s holiday season officially kicks off this Saturday, Nov. 18, and continues through December with a full calendar of festive activities for locals and visitors. From a sunset tree-lighting ceremony to start the season, followed by a holiday parade, four weekly Stag & Doe nights of retail promotions and strolling Santas, plus the long-awaited return of the Holiday House Tour, the neighborhood will be full of holiday fun for young and old.

The lights get turned on at the annual Circle of Trees event, 5:30 p.m. Saturday at the Woodmere Art Museum, 9201 Germantown Ave. The museum’s director, William Valerio, will flip the switch to illuminate trees around the museum. Anne McNiff, executive director of the Chestnut Hill Community Association, a co-sponsor of the event, expects “lots of really cute kids” who’ll get goodie bags, hot chocolate and cookies – plus an appearance from special guest Santa Claus. Free admission to the museum, and the grand opening of its holiday gift shop, follows. 

More family fun comes Friday, Nov. 24, when the Holiday Garden Railway is unveiled at the Morris Arboretum, 100 E. Northwestern Ave. The wintertime version of the popular model-train display features trains chugging over more than a quarter mile of outdoor track, winding through elaborate miniature villages adorned in seasonal lights and decorations. The railway runs 10 a.m. to 4 p.m. daily through Dec. 30.

Seasonal shopping along Germantown Avenue gets a kick start on Small Business Saturday, Nov. 25. This Saturday-after-Thanksgiving national promotion has become a new tradition here – a counterpart to the big-box-store commotion of Black Friday. In recent years, the event “has been a terrific way to highlight the importance of shopping small and local,” said Courtney O’Neill, executive director of the Chestnut Hill Business District. Santa and costumed Mummers will mingle between noon and 3 p.m.

A little farther down the Avenue, Mt. Airy merchants will host their own Small Business Saturday event, the Go Mt. Airy Shopping Crawl. Look for special promotions and refreshments, and pick up a Shopping Crawl Passport at any one of 27 participating shops and restaurants. Stop by to collect eight or more stamps from these businesses for a free Mt. Airy-themed holiday ornament. Details are at mtairycdc.org. 

Chestnut Hill’s first Stag & Doe night – the decades-long tradition of evening holiday shopping along Germantown Avenue – will be Wednesday, Nov. 29, then December 6, 13 and 20. Many shops will extend their business hours, with activities from 5 to 9 p.m., and the Chestnut Hill Parking Foundation will offer free parking in its six public lots all day and night each Wednesday through the 20th.

Many local retailers plan holiday specials as well as complimentary drinks and snacks for the Stag & Doe crowds. There’ll be more music along the Avenue, and if you haven’t seen him already, Santa will be back each Wednesday from 6:30 to 8:30 p.m.

“Stag & Doe is really when foot traffic picks up,” said Susanna Forjohn, who has presided over 29 holiday seasons at her boutique Quelque Chose. “People will come out with their friends and have dinner. The Avenue looks so pretty with the holiday decorations, and it’s bustling and festive.”

And look over there – it’s Santa Claus, the hardest-working man in Chestnut Hill, in the Community Holiday Parade on Saturday, Dec. 2. He’ll be joined by the Phillie Phanatic, marching bands, horses and a fleet of antique cars and fire trucks. You’ll see neighbors representing a variety of local groups as well.

“We encourage groups of people to be in the parade! But we also really encourage the community to come out and line Germantown Avenue to watch,” said McNiff of the Community Association, which organizes the yearly parade. Fans will have photo ops with Santa and the Phanatic along the route, which stretches along Germantown Avenue from Chestnut Hill Avenue to the Market at the Fareway, below Southampton Avenue. The parade begins at the top of the hill at 9 a.m. The rain date is Dec. 16.

December 9 marks the return of the Holiday House Tour, billed as “Philadelphia’s longest-running holiday tour.” The popular event, also sponsored by the Community Association, is now in its 27th year, following a three-year pandemic hiatus. The list of houses to be seen is closely guarded until the day of the tour.

“We have some really interesting architecture to see, and the opportunity to see these houses decked out in holiday decorations – some are way over the top and some are very elegant and understated,” McNiff said. “People often get inspired with decorating ideas.”

Refreshments and live music will be offered at each house. Tickets start at $45 at chestnuthill.org, and include discounts to select local restaurants, as well as free travel on a trolley that stops along the Avenue and at each home on the tour. 

On Dec. 16, Decemberfest: Made in Mt. Airy brings the party down to Lovett Park by the public library at 6945 Germantown Ave. It’s billed as a “first annual” maker’s market, offering locally made gifts and crafts, food, drink and live music from 11 a.m.-4 p.m. Santa will make the scene from noon-3 p.m. Rain date: Dec. 17.