Holiday Date Night in Philly: Guide to a Romantic Night Out

It's Cuddle Season!

Let’s be honest – the days are getting colder, the nights are getting longer, and finding someone to spend your nights out on the town or cozied up with is starting to sound better and better. If you’re looking for some cute date night ideas this holiday season in Philadelphia, search no more!

Watch a Tree Lighting Ceremony!

Tree Lighting Ceremony City Hall Philadelphia

Oh Christmas Tree, Oh Christmas Tree!

Here is a simple, yet festive, activity for the two of you to share! Fill up your mugs with hot coffee, cider, or something stronger (wink, wink), grab your favorite blankets, and head on over to Rittenhouse Square, City Hall or the Delaware River Waterfront for one of the Tree Lighting Ceremonies around the city! Enjoy caroling, live music, or visits from Santa, as crowds of cheerful people gather together in the icy air. There is just something about the energy of the city during the holidays that makes you feel alive and what better way to mark the start of the holiday season!

Some of my Favorite Tree Lighting Events are listed below:

Rittenhouse Square Annual Tree Lighting: Wednesday, December 7th, 2022

Blue Cross RiverRink Winterfest Tree Lighting: Friday, December 2, 2022

Dilworth Park Holiday Tree Lighting at City Hall: Thursday, December 1, 2022

Enjoy Cocktails at Rouge98's Winter Lodge

Espresso Martinis >>>

Hehe, now that I got your attention — start, end or spend your whole night cuddled up with your S.O. in the outdoor winter cabin themed area of Rouge98’s restaurant & bar. Located in the perfect little spot directly on Rittenhouse Square, you can enjoy the bustling atmosphere while getting closer to each other or pop in and grab a delicious drink (I recommend the above^^) before heading out to your next holiday event on your special little date night

Rouge 98 Winter Lodge

Spend an Evening in a Cozy Winter Cabin

The Rental Cabins at Blue Cross RiverRink are a unique way for the two of you to hang out on the town, but also have your own personal area among a cute little winter wonderland along the Delaware River Waterfront. Each cabin is fully decorated to make you feel like you have been plopped right into a scene from a Hallmark movie; stone fireplaces, antler chandeliers, fuzzy blankets & pillows, and other holiday décor occupy every little nook. Enjoy warm food and beverages, firepits, arcade games, and ice skating as well as views of the giant Holiday Tree & Ferris Wheel. Single cabins can fit as many as 8 people, so you also have the option to make it a double, triple or group date night for you and your friends!

P.S. There are plenty of photo-ops here

Rent a Winter Cabin!

Make Reservation for a Holiday Themed Bar!

Ok ok, I know sometimes these holiday pop-up spots can seem a little touristy...

But if you’re like me and can’t resist trying these kinds of restaurants & bars out at least once for the experience, read on! In my opinion, these pop up bars are the perfect opportunity to immerse you and your special friend directly into some festive, holiday spirit and either way you’ll both enjoy seeing the over-the-top, photo-worthy food and drinks!

Popular spots to try:

Craftsman Row Saloon’s Christmas Wonderland (pictured): 112 S 8th St, Philadelphia, PA 19107

Tinsel a Christmas Bar: 116 S 12th St, Philadelphia, PA 19107

Uptown Beer Garden’s Grinch Bar: 1500 John F Kennedy Blvd, Philadelphia, PA 19102

Craftsman Row Instagram

Spend a Cozy Night In!

I know you were both thinking it!

Instead of worrying about what reservations to make, what to wear, or whatever a night on the town could potentially hold… take the opportunity to spend a relaxing evening together at home on your own couch, in your PJs with your cats. Bust out the decoration bins, throw on a movie, light the candles, set up the tree, make hot chocolate with too many marshmallows, pour the wine… you know the drill. Do whatever your little hearts desire and have no shame in the stay home game!

Here are some of my favorite at home activities:

Puzzles!! Puzzles are so underrated and who doesn’t love the satisfying feeling of completing one?? Especially the 100+ pieces kinds.
Baking, of course!
Make your own pizza’s together!
WNRS card game – a personal favorite card game of mine for all year round. If you’re ready to get closer to each other on an emotional level, this will do the trick (iykyk)!!

Holiday Date Night in Philly: Guide to a Romantic Night Out

It's Cuddle Season!

Watch a Tree Lighting Ceremony!

Oh Christmas Tree, Oh Christmas Tree!

Enjoy Cocktails at Rouge98's Winter Lodge

Espresso Martinis >>>

Spend an Evening in a Cozy Winter Cabin

Make Reservation for a Holiday Themed Bar!

Ok ok, I know sometimes these holiday pop-up spots can seem a little touristy...

Spend a Cozy Night In!

I know you were both thinking it!

Follow us

Curated by

Philly Feeling

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Holiday Date Night in Philly: Guide to a Romantic Night Out

It's Cuddle Season!

Watch a Tree Lighting Ceremony!

Oh Christmas Tree, Oh Christmas Tree!

Enjoy Cocktails at Rouge98's Winter Lodge

Espresso Martinis >>>

Spend an Evening in a Cozy Winter Cabin

Make Reservation for a Holiday Themed Bar!

Ok ok, I know sometimes these holiday pop-up spots can seem a little touristy...

Spend a Cozy Night In!

I know you were both thinking it!

Follow us!

Follow us

Curated by

Philly Feeling