Philadelphia undergoes a transformation during winter, offering locals and visitors a unique array of experiences, from historical tours to local events. Embrace the chill as the city illuminates with festive lights, radiating holiday cheer. Winter in Philly reveals a captivating side for newcomers and long time residents alike. So, whether you’re looking to settle down and buy a home in Philadelphia, or possibly rent an apartment downtown, this Redfin article is your insider’s guide to winter delights in Philly, whether you’re seeking indoor or outdoor activities.
1. Take a sip-and-paint class
Demi from Stir Up The Paint shares, “My favorite winter activity is of course teaching Stir Up the Paint Events at Tapster. We host paint and sip events, where a master artist walks you through a painting during a two hour event and you take home your masterpiece. No judgments, no critiques—just pure fun. Events occur every Thursday from 7-9 pm, and on Saturdays and Sundays from 1 pm to 3 pm. We create diverse winter landscapes and Philadelphia-specific imagery during our painting sessions. Our generous hosts at Tapster provide a Self-Serve Tapster bar, an innovative concept in the Philly area. You can sample a variety of beverages and then self-pour your favorites after sampling. After these events I love to catch dinner (or lunch) at one of many sushi restaurants in Center City, my new favorite is Kura Revolving Sushi Restaurant. I especially love the little robot that drops off your soft drinks.”
“A great wintertime activity in Philadelphia is strolling the quaint streets and alleyways of Society Hill and Queen Village,” shares Dr. Michael Schatz from Philadelphia Jewish History Tours. “These neighborhoods were once Philadelphia’s immigrant Jewish Quarter a century ago. Today they have been restored as a premier, thriving and eclectic urban neighborhood. There are hidden in plain sight passageways and courtyards, and along S. 4th Street where pushcarts once reigned are independent shops and restaurants of all types.”
3. Walk the Morris Arboretum & Gardens
Bryan Thompson-Nowak, Director of Education at Morris Arboretum & Gardens says, “My favorite winter activity is taking a walk at Morris Arboretum & Gardens and appreciating the beauty of our amazing trees without leaves. The branch structure is exquisite, the winter light is magical, and an added bonus is that you can spot wildlife like woodpeckers and songbirds more easily.”
“My favorite winter activity is to get lost in the city lights, found in its energy and warmed in its
cafe’s and cocktail bars,” shares Kerri Marin from Philly Yard Bar. “Every side street offers a new beverage adventure, tantalizing the taste buds with diverse flavors. From coffees and lattes to crafted cocktails and wine. In the city, I enjoy savoring the art of beverage making.”
5. Fun and views by the Delaware River
“Our favorite winter activity in Philadelphia is the Independence Blue Cross Riverrink Winterfest,” says Monique West, Owner and Blogger of Traveling the West Way. “This event is beautifully situated along the Delaware River. There’s fun activities for everyone including ice skating, rides and games. And when we’re tired from a long day of fun, we can relax by one of the many fire pits with a cup of delicious hot chocolate and enjoy the magnificent city views.”
6. Go to a sports event
“Winter in Philly brings the thrilling sports scene alive,” says Mandy Brown from SuiteHop, a place to find premium tickets for events. “My favorite winter activity is sitting courtside seats for the 76ers, experiencing the intensity of glass seats for the Flyers, or enjoying the luxury of a suite for either team at the Wells Fargo Center. Being right in the action or enjoying the premium comfort turns these games into the ultimate winter fun, perfectly capturing Philly’s passion for sports.”
7. Play tennis at a club
“My favorite activity is to get into the tennis clubs and participate in clinics to get ready for the Spring season,” shares Steve Chagnon from Philadelphia Tennis League. “We can’t wait for the Spring when we can get back to the free outdoor courts to play some competitive tennis.”
8. Walk the Wissahickon trails
“One of my favorite things to do during the winter in Philly is walking the trails of the Wissahickon with my dog Gus and daughter LaLa,” says Jonene Lee, Owner of the NoName Gallery. “There’s a local artist, @wissmonsters, who does artwork on rocks and hides them all over the trails throughout the Wissahickon. We have a ton of fun finding them. Longwood Gardens is always a fun time for us in the winter as well.”
9. Explore Peddlers Village
“An interesting place that is located just north of the city in Lahaska, that holds many winter events in the Peddlers Village,” Suggests Allie from Northeast Allie. “This unique place has a very whimsical feel to it with a variety of cute shops, restaurants, and a multitude of fun activities. Some of their festivals that they hold this time of year include Fire & Frost Fun, Dueling Pianos and Desserts, Village of Chocolate, and even their spectacular Comedy In The Village. It is the perfect place to enjoy winter festivities.”
10. Eat through the indoor Reading Terminal Market
“During the winter time, I love getting to wander through the aisles of Reading Terminal Market and let my cravings for the huge variety of food run wild when in Philadelphia,” shares Kate Thompson from The Pink Chickadee. “Reading Terminal Market offers delicious and diverse cheap eats alongside fine goods to take home, too. With its proximity to many of Philadelphia’s major sites in Center City, I love getting to stroll through Philadelphia City Hall and LOVE Park without the crowds.”
11. Visit the waterfront
“The waterfront area has developed so much over the last ten years, and though it explodes and comes to life every summer as people flock to the water, it is often neglected in the winter,” says Liz Boleslavsky from Fringe Bar. “There are so many fun activities to still do on the waterfront in the winter. Winterfest is a great example of how the waterfront transforms for the season.
Fringe Bar itself gets very cozy in the winter, and it’s so nice to come here and play quizzo on Wednesdays. Anything with a fire-pit and a view, and boozy hot chocolate has my name on it. I think it’s just really great to see how different spaces get activated and how they engage guests in the times where people mostly stay indoors.”
12. Go to the zoo
Artist and Event Producer, Stacey Wilson from Flygirrl recommends, “One of my favorite winter activities in Philly is to make a big thermos of some hot tea or coffee and go to the Philadelphia Zoo for their always unique, annual winter exhibit. It’s always fun to walk around for the day and visit the beautiful animals but you also get to experience an exhibit which currently happens to be Trolls: Save The Humans. They are enormous and made from repurposed wood. Its mission is to inspire humans to take better care of Nature. It kicks off in February and I can’t wait to go see them.”
13. Visit a indoor pool
Ashley Albrecht of Albrecht Events says, “My favorite winter activity in Philly is an opportunity to warm up by the pool on the 57th floor of the Four Season’s Philadelphia. The stunning views of the city skyline in the lap of luxury make me feel restored. This is a cozy and luxurious escape right in the city that I love so much and call home.”
“The fun in Philadelphia doesn’t stop when the sun goes down. There are so many places to enjoy Philly’s nightlife, like the Assembly Rooftop Lounge at The Logan, bowling at Lucky Strike, and speakeasies like Hop Sing Laundromat,” says Michael Chapaloney, Executive Director of Pennsylvania Tourism.
16. Go to LOVE Park for the holidays
“A magical place I love to explore during the winter in Philadelphia is the Christmas Village at LOVE Park, which is known as a holiday market inspired by traditional German Christmas markets,” shares Grace Loemba Ndllo, Owner of Everlasting Weddings By Grace. “My husband and I enjoy taking our two kids there to enjoy the carousel. You can also find crafted holiday gifts, ornaments, and delicious homemade treats.
For couples who want to enjoy winter in Philadelphia, the Christmas Village is also a nice place for couples to enjoy a winter date night, and a couple of blocks away couples who are more into sports can find the Blue Cross River Rink.”
17. Ice skating Dilworth Park
“Braving the cold is worth it for the outdoor activities in Center City’s parks. Ice skating in Dilworth Park is a holiday favorite when you’re surrounded by the merry festivities of the Christmas Village at Love Park and City Hall,” says Michael Chapaloney, Executive Director of Pennsylvania Tourism. “Another festive favorite is Franklin Square, which is decked out with twinkling lights, a carousel, and even a mini golf course.”
“Philly is full of cultural hotspots, museums, and world-renowned institutions, with the Parkway Museum District at the heart of it all. The Barnes Foundation is a must-visit stop on the Parkway. The museum’s impressive collection has works from famous artists like Picasso, Matisse, and Renoir, and special installations from artists across the globe,” says Michael Chapaloney. “If you’re looking for a museum to visit with the kids or kids-at-heart, The Franklin Institute is one of the oldest science museums in the US, and it continues to excite visitors with new and interactive exhibits.”
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Holly is part of the content marketing team and enjoys writing about home improvement and lifestyle. Her dream home would incorporate both an industrial and biophilic design.
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