The Ultimate Guide to Holiday Shopping on the Hill

Chestnut Hill’s walkable shopping district is charming year-round – but wait until you experience it during the holidays. Twinkling lights, festive window displays and strolling carolers spread good cheer up and down Germantown Avenue, making it a magical destination for seasonal shopping and celebrating.

Here’s the star on top: This Philadelphia village is home to more than 125 independently-owned retailers, from artisan bakeries to boutique toy stores, so it’s a one-stop spot for unforgettable gifts and hosting essentials. Even better, the shops on the Avenue stay open late – and treat you to hot cocoa, wine tastings and seasonal goodies – during Stag and Doe Nights on Wednesdays in December!

Get in the holiday spirit (and get all your shopping done) with a little help from this guide to one-of-a-kind stores and seasonal attractions on the Hill:

Cherished Toys

Villavillekula, named after the fictional home of Pippi Longstocking, sells a playful array of children’s apparel and toys that reflects the zany spirit of its literary inspiration. Buy fun surprises like wearable dinosaur tails and umbrellas that change color in the rain, along with hand-knitted sweaters, holiday bowties and more adorable fashions for kids from newborn to 10 years old. And don’t forget your fur children! Stop in The Bone Appetite for holiday treats, durable toys and cozy new beds for your family pet. If you like dressing your pup up, you won’t be able to resist getting a new dog sweater – or Philadelphia Eagles jersey – for the season.

Grown-Up Gifts

Whether looking for holiday bling or a gift inspired by your loved one’s alma mater, you’ll find memorable presents for adults on your list all throughout Chestnut Hill. Start at Serendipity to peruse a wide assortment of items including vintage university pendant pillows, colorful soaps and bath bombs, wall-mount bottle openers and Philadelphia-inspired gifts galore. The store sells locally designed holiday cards, too! If handmade is what you’re after, also visit Windfall Gallery, which offers craft jewelry, glass art and fair-trade goods made by more than 150 artists from across the globe. You can pick out the perfect pair of sterling silver earrings for your best friend or buy hand-carved soapstone hearts as gifts for co-workers or teachers.

Spend time in Chestnut Hill Jewelers to choose from fine jewelry featuring precious metals and stones. With an eye for quality and craftsmanship, the specialists at this boutique will help you find a design perfectly suited to your partner’s tastes. Vintage lovers will also appreciate their well-curated selection of estate jewelry on consignment. On the hunt for an upscale men’s gift? Style by Blain is a must-visit. This footwear boutique features high-end brands including Alden and Paraboot, and the owner makes a point to personally test styles for comfort and quality before stocking them. Built to last a lifetime, a pair of shoes from here is one of the most useful gifts a guy can receive. (If you’re looking for a fashionable women’s gift, check out these 13 trendy boutiques on the Hill for every style.)

Next up, flip through used and new albums at Hideaway Music to find special sounds for the vinyl aficionados in your life. This organized independent record store carries every genre from classic rock to indie pop, plus giftable box sets honoring legends like Bob Dylan and Jimi Hendrix. You can also invest in a variety of quality vintage audio equipment, cleaned and carefully inspected by the shop’s experts.

Seasonal Sweets

’Tis the season for shareable treats, and there’s no shortage of homemade goodies on the Hill! Put together a platter of classic German cookies from Bredenbeck’s Bakery – also known for its spiced gingerbread (and impressive gingerbread window display) – or pick up one of their glazed rum rings to make your coworkers’ holiday dreams come true. Then make another sweet stop at Night Kitchen Bakery for Christmas morning delights including cinnamon buns, scones and sour cream pecan coffee cake. Night Kitchen also bakes up festive Yule logs (a.k.a. Buche de Noel) this time of year, and their cheesecakes are a crowd-pleaser no matter the occasion.

Refuel with sandwiches and soup at Baker Street Bread Co., and pick up freshly-baked dinner rolls, challah or baguettes for your holiday meals while you’re there. Need a quick hostess gift? Baker Street’s scrumptious pumpkin cranberry bread will do the trick. The eatery also sells premade cookie dough, so you can bake at home with your family – minus the mess of flour in the kitchen. If you’re craving chocolate, or looking for another easy edible gift, go to Made By ME Candies in Market at the Fareway. Chocolatier MaryEllen Salamone will be there decorating mouthwatering gourmet chocolates, which you can buy in assorted boxes for anyone left on your holiday list. Her peppermint bark and hot chocolate on a stick also make great stocking stuffers!

Holiday Hosting

You’ll need more for your gatherings than just dessert, so let the specialty stores on the Avenue help you with party prep. For décor, head to Robertson’s Flowers & Events, where you can gather holiday trimmings to adorn your home from your tree to your tabletop. Have fun selecting stylish ornaments, classic nutcrackers and cozy Frasier Fir candles, and be sure to order a festive floral centerpiece. If you’re celebrating in someone else’s home, come prepared with a special offering from Threadwell, which specializes in custom monogramming. This shop is a destination for all kinds of personalized presents, but its stock of nostalgic Christmas linens, unbreakable stemless wine glasses and customizable serving trays makes it a natural for thoughtful hostess gifts.

Every gathering calls for a cheese platter, and you can curate the makings of a delicious one at Evergreen Cheese Shop. This neighborhood institution has been in Chestnut Hill for 55 years, and the knowledgeable owner will be happy to help you sample and select gourmet cheeses from porter cheddar to garlic basil gouda to cave-aged gruyere. Continue your culinary journey at The Spice Rack to complete your platter with small-batch chutneys and spreads for guests to try – their blue cheese, honey & shallot spread is a popular pick. Catering to everyone from novice cooks to trained chefs, this shop also carries a wide selection of specialty smoked salts, vinegars and olive oils from Napa and Sonoma, and artisan hot sauces of all spice levels.

Family Festivities

Take a break from shopping and join in beloved Holidays on the Hill traditions all season long. Throughout the month of December, Santa makes multiple stops in Chestnut Hill, including the Market at the Fareway and Laurel Hill Gardens, where kids can share their wish lists and snap photos with the big man in red. Santa will also greet children during the anticipated Chestnut Hill Community Holiday Parade, which brings marching bands, floats, antique cars and more holiday fun down Germantown Avenue for the whole family to enjoy.

And don’t miss a neighborhood favorite, The Holiday Garden Railway at Morris Arboretum, where you and the kids will be enchanted as model trains chug along a quarter-mile track, surrounded by a miniature holiday village adorned with thousands of lights!

Click here to find more shops and attractions for all ages in Chestnut Hill.

Photo: Woodmere Art Museum by Darryl Moran