13 Philly Spots for Holiday-Cheer-Filled Engagement Photos

Now all we need is some mistletoe.

holiday engagement photos

A Longwood Gardens winter engagement photo session / Photograph by RingShot Photography

Winter may not be the most popular season for weddings, but it is a pretty spectacular time of year for engagement photos (and proposals, natch). With ice-skating, Christmas tree decorating, hot chocolate sipping, and so much more, there are plenty of ways to bring the holiday spirit to your winter engagement photos. Here are some of the (many!) amazing places to do just that around Philly. And if we missed the spot where you snapped your festive engagement photos, share them with us at kschott@phillymag.com.

Terrain at Styer’s

holiday engagement photos

Photograph by Hilary Myers Photography

Though Terrain Gardens at Devon Yard is totally picture-perfect for weddings, the original Styer’s location in Glen Mills is your best bet for engagement photos — particularly of you and your S.O. cozying up around an outdoor fire pit.

Dilworth Park Ice-Skating Rink

dilworth ice skating rink engagement photos

Photograph by Werth Photography

Officially called the Rothman Orthopaedics Ice Rink (good to know if you’re Googling for hours), Center City’s main ice rink is a chill place to nab some action shots before warming up over decadent cups of hot chocolate. While you’re there, check out the rest of the fun, too.

A Christmas Tree Farm 

christmas tree farm proposal

Stevie Snyder (left) and Casey Hoffmann / Photograph by Heather McBride Photography

Okay, so this particular — and particularly adorable — photo was from a proposal, but you get the point. A Christmas tree farm, like Exley’s in Sewell, is a truly festive place to photograph your special moments during the winter. (It’s even better if you can decorate a tree with tinsel, ornaments, garlands and more!) Still scoping out locales? Consult our roundup of 24 places near Philly where you can get your tree.

Addison Street 

addison street proposal

Mosum Shah and Umang Jain / Photograph by Martin Reardon Photography

The trees on the 1700 block of Addison Street are technically strung in white all year long, but they feel especially festive come winter — and draw folks to pop the question and snap engagement photos amid the lights.

Peddler’s Village

peddler's village proposal

Angelena Minniti and Mike Stampone / Photograph by Alex Subers

Consider this charming New Hope destination the closest thing in the Philly area to the North Pole. With plenty of festive light displays and decor, there’s a new backdrop around every corner for engagement photos, proposals, anniversary portraits — and any other snapshot that needs a helping of holiday cheer.

Washington Square Park 

washington square park engagement photos

Photograph by Love Me Do Photography

There’s something about the combination of brick walls, black shutters, and snow-covered bushes that feels quintessentially “winter in Philadelphia.”

The Dandelion 

dandelion restaurant engagement photos

Photograph by Nina Lily Photography

Red leather booths, a crackling fireplace, a touch of tartan, and plenty of holiday greenery and decor make this Rittenhouse restaurant the perfect place to cozy up for an e-sesh (or even hold your elopement dinner, if you’re thinking of the future). Want to lean into the season even more? Consult our list of festive bars in Philly for some over-the-top settings.

Rittenhouse Square 

winter engagement photos

Cheryl Acerbo and Patrick MacMillan / Photograph by Emily Wren Photography

Yes, it’s obvious. But it’s obvious for a reason, amirite?

The Poconos 


Marissa Moyer and Todd Danner / Photograph by Emily Wren Photography

Seeking a winter wonderland backdrop? Look no further than the wooded forests of upstate PA — like this e-sesh at Skytop Lodge and its snowy surroundings.

McGillin’s Olde Ale House 

winter engagement photos

Kim Graf-Offner and Greg Offner, Jr. / Photograph by Morby Photography

It’s extremely Philly, and it’s extremely tricked out around the holidays — so it’s no wonder this iconic local watering hole continues to be a magical locale for meet-cutes, not to mention proposals and engagement photos.

Longwood Gardens

Longwood gardens

Allyson Hawk and Tyler Shotto / Photograph by Jessica Manns Photography

Because the poinsettias perfectly match your dress.

18th Century Garden

18th Century Garden

Photograph by RingShot Photography

Sure, the Old City landmark is pretty when in full spring bloom — but there’s something serene and special about strolling amid the plots and latticed gazebo in winter, too.

The Steps of Anthropologie Rittenhouse


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Now just imagine you and your partner-in-life posing on those beautifully decorated steps.

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