21 Fantastic Things to do this Winter in Philly
Disclaimer: We are not paid to promote any restaurant, hotel, activity, product, or attraction. All opinions are subjective and based on our personal experience. Your experience may be different.
16. Enjoy a free concert via the world’s largest operating pipe organ
Macy’s Center City is located in the beautiful historic Wanamaker Building, one of the country’s first department stores. Every day at noon you have the unique opportunity to listen to the world’s largest playable pipe organ. This tradition dates back to 1911.
During the Christmas season, you will be treated to a wonderful LED show, with live music via the Wanamaker Grand Organ accompanying noon shows. I highly recommend getting out here for this festive and free show: it’s my favorite holiday event in the city.
The department store itself is gorgeous. It’s worth visiting, if nothing else just to admire the beautiful architecture. If you are a fan of 80’s movies, you will likely remember seeing this beautiful building somewhere. The cult classic Mannequin (one of my personal faves) was filmed on-site!
Update: This Macy’s closed in spring of 2025, but the Christmas show tradition still lives on.
- Location: 1300 Market Street
- Show times
17. Relax fireside with a hot drink at Winterfest
Winterfest at Penn’s Landing is the place to be as soon as December rolls around. With a picturesque riverside ice rink, hot drinks and treats from The Franklin Fountain, fire pits, a warming house with cozy couches, cozy swing and rocking chairs complete with thick blankets, and special seasonal events, there’s plenty of festive fun to be had here. The place is bustling from opening day in late November through early March. Even if you are not skating, it’s a great place to enjoy the holiday ambiance.
Admission to the fest is free even if you are not skating which is nice. Take a cozy seat inside the lodge, wrap yourself with a blanket on a cozy rocking chair, or enjoy a warm fireside seat. Head over to The Franklin Fountain and grab a hot cocoa, hot tea or coffee, or even a scoop of ice cream to accompany you as you watch the skaters glide by.
- Location: 101 S. Christopher Columbus Blvd
18. Get lost in a local bookstore
Browsing bookstores is always a fun way to escape frosty temps for a bit. I actually love visiting independent bookstores as they are so rare today. As everywhere becomes a Barnes and Nobles, it’s nice to see these small shops still surviving.
Bibliophiles will want to check out Book Trader located in Old City. This independent shop features 2 floors jam packed with both new and rare finds. Also, there are lots of records, DVDs, and even songbooks to browse through. You will find tons of great deals here including a $1 section. Mostly Books located in Queens Village is another local gem.
Address: 7 N. 2nd Street
19. Observe cats for a great cause at Kawaii Kitty Cafe
Update: This cafe sadly closed during Covid. Le Cat Cafe took its’ place.
Since opening in Taiwan in 1998, cat cafes have continued to sprout up all over the world. In the US, the first cat cafe opened in Oakland back in 2014. Philadelphia’s first cat cafe, Kawaii opened in 2016 in the Queens Village neighborhood. Never heard of a cat cafe? Basically it’s a place where people pay to be in a room surrounded by cats (all available for adoption). Even if you have no intention of adopting, knowing that your money goes towards the cat’s care is a reward in and of itself. A bit pricey, but I think it is worth it as a cat lover.
To date many hundreds of cats have been rescued from possible euthanasia. Kawaii works with the Philadelphia Animal Welfare Society to house cats in a safe environment until they are adopted. This place is super busy, and thus, reservations often need to be booked several days in advance.
Location: 759 S. 4th Street
20. Plan a brunch date
I love a great brunch when it’s cold out. Wintertime is a great time to check a new restaurant off your list. First off, it’s much easier to walk in without a reservation during the slower season. Second, a hot brunch is just so much more satisfying when it’s super chilly outside. Endless coffee, a delicious hot stack of specialty pancakes, a cozy setting – it just somehow seems more of a treat this time of year.
You will find lots of great choices throughout Old City and Center City to choose amongst. Parc in trendy Rittenhouse Square is one of the most sought after places to brunch in the city. This beautiful French restaurant overlooking Rittenhouse Square offers the perfect ambiance for a date. I enjoyed the Vol-Au-Vent (pic above). Other great choices include Farmica in Old City (try the Caramel Apple French toast!) and Sabrina’s Cafe (try the Mexi Scramble).
21. Stroll around Longwood Gardens
Although it is located an hour outside of the city, the drive to Longwood Gardens is well worth the hassle in my opinion. This is one of the most gorgeous gardens I’ve visited. Most likely it will be too cold to enjoy the outdoor gardens, however, the conservatory is warm and alive with fresh tropical plants all year round. It’s like taking a mini escape to paradise.
Christmas time, I recommend booking tickets to “A Longwood Christmas,” a special celebration featuring dozens of Christmas trees, festive fountain shows, live music performances, and thousands of colorful poinsettias. Check out some gorgeous pics from my visit. February & March is Orchid Extravaganza featuring thousands of colorful orchids.
- Location: 1001 Longwood Rd, Kennett Square, PA 19348
- Pricing: $45 for adults, $25 for kids ages 5-18 (timed tickets required)
- See what’s in bloom
More winter fun!
Everyday Activities:
- Bowling (Check out North Bowl in trendy Fishtown)
- Get a massage (Really, a treat anytime of the year!)
- See a movie at the Philadelphia Film Center (they show classics on Thursday nights)
- See a Broadway production at the Kimmel Center. Check out this season’s lineup.
Annual Events to Check Out
- A Longwood Christmas
- Christmas Village at Love Park
- Winterfest
- Macy’s Light show
- New Year’s Eve fireworks on the Riverfront
- Center City Restaurant Week
- Philly Theater Week
- Philadelphia Home and Garden Show
- Philly Craft Beer Festival
- St. Patrick’s’ Day Parade
