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 26th, 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.

East Passyunk

East Passyunk Avenue decked out for holiday shopping / Photograph by Jared C. Wood

Kick off the season on Small Business Saturday (November 26th) 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 and new sister store Tiny Tildie’s, the sustainable Good Buy Supply, ‘80s and ‘90s vinyl haven Latchkey, Occasionette and more. Plus, Nice Things Handmade is hosting their 12th annual ornament show featuring 30 local artists.

Grab a punch card from November 26th to January 2nd. 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 a weekly drawing. (Or send proof that you spent $100 to them online to be entered.)

On December 10th, there will be a “shop and stroll” with sidewalk sales, pop-ups and the Hot Chocolate Crawl.

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, photos with Santa (December 1st, 3rd, 4th and 8th) and other events. Come to the Singing Fountain on December 1st for the tree lighting and holiday celebration from 5 to 7 p.m. Return on December 18th for a Hanukkah celebration with the South Philadelphia Shtiebel. Kids can also drop off letters to Santa at the North Pole Mailbox located at the Singing Fountain starting on November 26th.

Chestnut Hill

Photograph courtesy of Chestnut Hill Business District

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 26th), Chestnut Hill will host Mummers and carolers from 1 to 3 p.m., Santa visits from noon to 3 p.m., and carriage rides — 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.

Then, on December 10th at 9 a.m., come for the holiday parade featuring floats, marching bands, antique cars, Santa and the Phanatic.

You can also see Santa as the Market at the Fareway on Saturdays from noon to 2 p.m. Not to mention parking will be free at the public lots all season long.

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).


Photograph by M. Kennedy for Visit Philly

Head to Main Street to check out the dozens of small businesses. On November 26th, shop specials for Small Business Saturday and stick around to see the businesses all lit up for the holidays. On Thursday nights, come for Holiday Light Nights with food and drink deals, shopping specials and live entertainment from 5 to 9 p.m. Even better, expect free Jolly Trolley rides up and down Main Street. Bring your pups for Santa Paws photo sessions at Pet Friendly Dog Bakery on December 4th. Then, on December 10th, 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 26th) with sales, pop-ups and special offers throughout the day. Be sure to sign up for the free Old City Holiday Pass on your phone to get special offers from shops, restaurants and museums through December 30th. (You’ll also be entered to win prizes, including weekly holiday prize packs and $500 in gift cards.) Old City shops also go all out with their holiday window displays, so be sure to stroll around and admire the decorations.

Stop by the Betsy Ross House on November 30th at 6 p.m. for the annual tree lighting including live performances and special guests. (You can also stream the tree lighting on Old City’s Facebook page.) Betsy Ross House’s menorah lighting will take place on December 18th at 4:30 p.m.

In addition to season-long specials, don’t miss the Old City Shopping Stroll on December 14th. The shops will stay open late (until 7 p.m.), you’ll get a free Old City tote bag with any purchase, and you can cap off your evening with a screening of How the Grinch Stole Christmas at Arch Street Meeting House.

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 Small Business Saturday deals on November 26th. Every Thursday, they continue their “Meet Me on South Street” series with themed shopping, food and arts experiences. (December’s theme is “Gifts under $25”.)

On December 3rd, 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. The afternoon will also include caroling with New Groove Music Studio and Nutcracker excerpts from Settlement Music School. Additionally, bring small toys and coats to donate for a community drive, and purchase cookies benefiting MANNA’s efforts to nourish those in need. Sisterly Love will host two more pop-up holiday markets on December 10th and 17th from noon to 4 p.m. at the Shambles.

On December 22nd, come to the Shambles for a menorah lighting and Hanukkah celebration at 5 p.m. They’re also planning a Kwanzaa display at Headhouse Plaza on December 26th.

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 29th at 6 p.m., they’ll light the tree with a celebration that includes free refreshments, performances, and special guests like Princess Belle.

On December 10th, check out the Northern Liberties Holiday Pop-Up Market taking over North Bowl with over 30 vendors, kids’ crafts, and photos with Santa’s scary counterpart Krampus. Speaking of Santa, you can brunch with him at Figo on Saturday, December 18th. The event includes photos with Santa, a cookie-decorating station and more. Or, if you prefer Elsa, Figo’s got her on December 10th and 17th for “igloo brunch” events.

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