Shop Hyper-Local With These Neighborhood Holiday Events

Get merry and support Philly businesses with these special shopping events on Small Business Saturday and beyond.

Festive holiday shopping around Philly / Photograph by Daryl Moran for Chestnut Hill Business District

This holiday season, beginning with Small Business Saturday on November 25th, neighborhoods throughout the city are getting festive and highlighting their unique businesses with pop-up events, loads of lights, Santa sightings and more. If you’re looking for extra merriment with your holiday shopping (a jolly trolley, perhaps?) hit up these Philly neighborhoods for everyone on your list.

Chestnut Hill

This charming neighborhood’s annual Holidays on the Hill is full of old-timey Christmas cheer. Think Victorian street carolers, horse-drawn carriage rides, and Santa visits. On Small Business Saturday (November 25th), Chestnut Hill will host Mummers from 1 to 3 p.m. and Santa visits from noon to 3 p.m. — along with plenty of shopping, of course.

Chestnut Hill’s popular annual Stag & Doe Nights will take place every Wednesday in December from 6:30 to 8:30 p.m. The events feature extended store hours, holiday specials, a roving brass quartet and free refreshments. You may even catch a glimpse of Santa strutting down the Avenue. Parking will be free at the public lots on these nights, as well.

Then, on December 9th at 9 a.m., come for the holiday parade featuring floats, marching bands, antique cars, Santa and the Phanatic.

And while you’re hanging around Chestnut Hill, head to Morris Arboretum to see the Holiday Garden Railway (even better if you can snag nighttime tickets to see it all lit up).

East Passyunk

small business saturday

Occasionette / Photograph courtesy of East Passyunk Business Improvement District

Kick off the season on Small Business Saturday (November 25th) with specials at boutiques up and down the Avenue. East Passyunk is home to some of Philly Mag’s favorite stores including the irreverent South Fellini (perfect for the Eagles fan on your list), Tildie’s Toy Box (giving out double Play Pass awards), the sustainable Good Buy Supply (giving out $5 coupons to the first 100 shoppers), vinyl haven Latchkey, Occasionette and more. Plus, Nice Things Handmade is hosting their 13th annual ornament show featuring local artists through January 12th.

Grab a punch card from November 25th to January 1st. Receive a punch for each $10 spent at participating businesses; once you get 10 punches, submit the completed card to one of the Avenue’s independently owned businesses to be entered to win a gift card in the prize raffle.

Aside from the shopping experiences, East Passyunk will be “Decking the Avenue” all season long with photo-worthy decorations and lights, pop-up musical performances. Come to the Singing Fountain on November 29th for the tree lighting and holiday celebration from 5 to 7 p.m.  There will also be photos with Santa that night. (If you miss out, he’ll be back on December 3rd, 14th, 16th and 17th.) Kids can also drop off letters to Santa at the North Pole Mailbox located at the Singing Fountain starting on November 29th.

Return on December 7th for a Hanukkah celebration with the South Philadelphia Shtiebel. And on December 9th, they’re bringing back the Hot Chocolate Crawl from last year! It’s what it sounds like: Restaurants and bars along the Avenue offer hot cocoa (and boozy alternatives) for a delicious addition to your holiday shopping.


The Manayunk Jolly Trolley / Photograph courtesy of Manayunk

Head to Main Street to check out the dozens of small businesses. On November 25th, shop specials for Small Business Saturday and stick around to see the businesses all lit up for the holidays. Be sure to vote for your favorite display in the “Manayunk Gets LIT” competition, where Main Street businesses deck their storefronts with thousands of lights for merriness and bragging rights. Voting runs through December 14th.

To make things a little easier, there will be free Jolly Trolley rides up and down Main Street. The trolley begins its run on November 30th and will run through December 23rd on Thursday and Friday nights (5 to 9 p.m.) and Saturdays from 1 to 9 p.m. Those nights, there will also be live entertainment on Main Street, including carolers, Santa, and the Grinch! (See the schedule online.)

Bring your pups for Santa Paws photo sessions at Pet Friendly Dog Bakery on December 2nd. Then, on December 9th, dress in your holiday best for the three-mile Rudolph Run.

Old City

Photograph courtesy of Old City District

Historic Holidays in Old City kick off on Small Business Saturday (November 25th) with sales, pop-ups and special offers throughout the day. In addition to neighborhood stores, a number of Old City restaurants have deals on gift cards — including Cuba Libre ($10 gift card for every $50 gift card purchased) and Positano Coast ($20 GC for every $100 GC).

Old City shops also go all out with their holiday window displays, so be sure to stroll around and admire the decorations. Vote online for your favorite between November 25th and January 1st — one voter at random will receive a $150 gift card to the participating Old City business of their choice.

Stop by the Betsy Ross House on November 29th at 6 p.m. for the annual tree lighting including live performances and special guests. Betsy Ross House’s menorah lighting will take place on December 10th at 4 p.m.

In addition to season-long specials, don’t miss the Old City Shopping Stroll on December 13th. The shops will stay open late (until 8 p.m.), you’ll get a free Old City tote bag with any purchase.

South Street

South Street tree lighting / Photograph courtesy of South Street Headhouse District

South Street is hosting holiday celebrations and shopping all season long, starting with the South Street Holiday Haul, which runs from November 16th through December 25th. Shop at their 40-plus small businesses for the chance to win a South Street shopping spree valued at over $200. For more chances to win, share a photo from your visit using the hashtag #SouthStreetHolidayHaul.

On December 2nd, come to the Headhouse Shambles starting at noon for the Mrs. Claus holiday market featuring Sisterly Love Collective, culminating in the annual tree lighting at 4:15 p.m. Sisterly Love will host two more pop-up holiday markets on December 9th and 16th at the Shambles.

On December 11th, come to the Shambles for a menorah lighting and Hanukkah celebration at 4:45 p.m.

Northern Liberties

Princess brunch at Figo / Photograph courtesy of Northern Liberties

NoLibs is getting festive all season long, starting with Black Friday deals at a selection of their small businesses. Then, on November 28th at 6 p.m., they’ll light the tree with a celebration that includes free refreshments, performances, and special guests like Santa and Princess Belle.

New for this year, Northern Liberties is hosting a Holiday Shopping Stroll on December 9th and 10th. Grab a map and punch card, then visit participating businesses to collect punches — no purchase required! Each store will also have fun surprises and events like discounts, free snacks, and demos. Shoppers that get six or more punches will be entered to win a special grand prize package. Of course, you can enter to win other prizes by shopping — for every $25 you spend you get entered for other prizes. Bring completed punch cards and receipts to the Northern Liberties Holiday Pop-Up Market at the Operator’s Club at the Piazza, also happening on December 9th and 10th.

That market will include local makers, plus a visit from Santa’s scary counterpart Krampus. For something less frightening, December 9th will also see igloo brunch with Queen Elsa at Figo at 11 a.m. and 1 p.m.

Looking for more? Check out our guide to pop-up holiday markets.