14 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 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 Properties

holiday engagement photos

Terrain at Styer’s / Photograph by Hilary Myers Photography

All three of the Terrain properties are picture-perfect for weddings — and engagement photos, too. The original Styer’s location in Glen Mills (above) might see you and your S.O. cozying up around an outdoor fire pit, while Terrain Gardens at Devon Yard has that beautiful nursery and seasonal installations. And at the new Terrain Gardens at DelVal? The outside ceremony garden or nursery are oh, so pretty this time of year. There’s a fee to hold a shoot at any of these locations and based on availability. Click here for more information.

A Christmas Tree Farm 

christmas tree farm proposal

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 22 places near Philly where you can get your tree.

Addison Street 

addison street proposal

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

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. A particularly popular spot? The gazebo, but of course. Advanced registration is required for photo shoots.

Washington Square

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 

The Dandelion

Photograph by Cheryl Betances 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). Advanced reservations for photo shoots are required. Want to lean into the season even more? Consult our list of festive bars in Philly for some over-the-top settings.

Rittenhouse Square 

Rittenhouse Square

Photograph by RingShot Photography

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

The Poconos 


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

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 (like this sweet one that was 40 years in the making!) and engagement photos.

Longwood Gardens

Longwood Gardens

Photograph by Jessica Manns Photography

Longwood Gardens goes all out for the season, decking its plants, trees, lawns — basically everything — with festive lights and decor. Advanced reservations for photo shoots are not required, though all photography must take place outside.

18th Century Garden

18th Century Garden

Photograph by Liz Gibbs Photo

There’s something serene and special about strolling amid the plots and latticed gazebo.

The Steps of Anthropologie Rittenhouse

Anthropologie steps

Photograph by RingShot Photography

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

Elfreth’s Alley

Elfreth's Alley

Photograph by RingShot Photography

Another obvious one. but it’s fun to play pretend with your S.O. and pose on the charming stoops, many of which are decorated with wreaths, garlands and more festive decor for the season.

LumiNature at Philadelphia Zoo

LumiNature at the Philadelphia Zoo / Photograph by Georgi Anastasov

The lights! The flamingo tree! Need we say more? (We do: Advanced notice is required for photo shoots, and the group must pay full admission.)

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