As the air turns crisp and the twinkling lights begin to glow, Chestnut Hill transforms into a true winter wonderland. Our little historic village bursts with charm, and it seems like every corner has something merry going on. Between nearly every boutique, café, and tree-lined street, you’ll find ways to soak in the joy of the holidays — and the good news is, we don’t even need to travel far. From enchanting tree-lightings to dazzling light shows and old-fashioned markets, here’s a roundup of holiday events within a 30-minute (or less) drive that you won’t want to miss.
Circle of Trees Celebration
One of the most beloved traditions kicking off the season is the Circle of Trees Celebration at Woodmere Art Museum. This free, family-friendly event brings together neighbors for hot chocolate, cider, cookies, and live music. Santa makes a dramatic entrance on an antique fire truck, and children can navigate a straw maze while waiting for the big tree lighting. The warmth of this gathering really sets the tone for the rest of the holiday season in Chestnut Hill.
Holiday Garden Railway at Morris Arboretum
Another Chestnut Hill gem is the Holiday Garden Railway at Morris Arboretum. A train display winds its way through a quarter-mile of miniature villages, natural foliage, and twinkling lights, all crafted from natural materials. During select evenings (Thursdays–Sundays), the Arboretum hosts ticketed nighttime tours with laser shows for an even more magical experience.
Stag & Doe Nights on Germantown Avenue
Every Wednesday between Thanksgiving and Christmas, Chestnut Hill comes alive with Stag & Doe Nights. Local shops stay open later, offering seasonal specials, and brass quartets serenade the Avenue. You might even spot Santa strolling by, and many of the stores serve complimentary treats — it’s the perfect evening to combine shopping, strolling, and savoring holiday joy.
Arts & Eats: Holiday Edition
On the first Friday in December, the neighborhood’s Arts & Eats evening gets a festive twist. Participating galleries and restaurants extend their hours, and there’s live brass music from 6–8 p.m. Santa joins in too, greeting families as they sip seasonal refreshments and explore local art.
Annual Chestnut Hill Holiday Parade
The Holiday Parade organized by the Chestnut Hill Community Association is a joy to behold. It features marching bands, antique cars, fire engines, horses — and yes, even the Phillie Phanatic makes an appearance. The parade travels down Germantown Avenue, ending at the Market at the Fareway, and community spirit is high.
Holiday House Tour
If you love architecture and decked-out decorations, the Holiday House Tour is for you. On this self-guided or trolley-assisted tour, you’ll explore some of Chestnut Hill’s most beautifully adorned homes, enjoy live music, and bask in the holiday glow. It’s a charming way to see the neighborhood through a seasonal lens.
Small Business Saturday in Chestnut Hill
On Small Business Saturday, the Hill really shines. Shoppers are encouraged to “Keep It on the Hill,” supporting our local boutiques and restaurants. From around noon to mid-afternoon, Santa strolls the Avenue, and Victorian-dressed carolers perform — celebrating the heart and soul of our community. Chestnut Hill
LumiNature at the Philadelphia Zoo
Just a short drive from Chestnut Hill, LumiNature at the Philadelphia Zoo is a dazzling holiday light show that delights visitors of all ages. This year’s event features more than a million lights forming whimsical wildlife scenes, Santa’s cozy Lodge, and a brand-new 110-foot “Pherris” (Ferris) Wheel that offers gorgeous views of the zoo and city skyline.
Christmas Village in Love Park
If you feel like venturing a little farther into Center City, Christmas Village in Philadelphia is a must-see. Modeled after traditional German holiday markets, this open-air event (at LOVE Park and City Hall) features 120+ wooden huts filled with handmade gifts, ornaments, and holiday treats. There’s also a new glowing German Christmas pyramid, a Ferris wheel, a carousel, and festive food — plus Santa in the Welcome Center for photo ops.
City of Philadelphia philachristmas.com
Wanamaker Light Show & Dickens Village
Another gem in Center City is the Wanamaker Light Show and Dickens Village, reimagined for the holiday season. The historic Wanamaker Building plays host to a nostalgic light show with performances on the famous organ, and friendly Victorian-style characters populate the Dickens Village. This event blends tradition, music, and architectural beauty to create a festive, free experience for all.
Why These Events Make Chestnut Hill’s Holidays Special
Each of these events reflects something uniquely Chestnut Hill or nearby — whether it’s the historic homes on Germantown Avenue, our deep-rooted love for local shops, or a passion for community traditions. They don’t just feel like holiday “things to do”; they feel like home. You can cup hot cocoa after watching a tiny train chug by, or pause mid-stroll on Stag & Doe Night to listen to brass music echo under the glow of storefront lights. For me, that’s what makes this season in Chestnut Hill so magical.
As you map out your holiday calendar, don’t forget to look for events near and far — from the gentle sparkle of Morris Arboretum to the grand lights of the Zoo, or the chatter of German holiday booths at Christmas Village. And hey, after you’ve soaked up all that festive cheer, maybe drop by John Kennedy Subaru for a little last-minute gift shopping (or at least to admire their holiday spirit — we always make our lot look merry and bright!). Here’s to a joyful, cozy, and community-filled holiday season in Chestnut Hill.
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