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15 Fun Things to Do in Philly this May!

Attending local events is not only a great opportunity to get off the couch and stop doom-scrolling or binge-watching Netflix, but an opportunity to connect with your community. Community is crucial to the Real Estate Relief team, and we are guided by our core value of Restoring Communities. When we participate in an event locally, it’s an incredible opportunity to connect with new members of our community and to support local businesses.

After welcoming the beautiful cherry blossom blooms this April, spring is officially in full swing and Philly is abuzz, enjoying the lovely outdoor spaces that our city has to offer. With street festival season approaching, there are countless opportunities for fun in the Philadelphia area this coming May. The Real Estate Relief team will definitely be doubling up on our festival attendance to make sure we can check out all of these amazing events!

Dining Under the Stars in Media 
May 3 - September 27
Each Wednesday, Media’s State Street will be closed to car traffic from Jackson Street to Orange Street, allowing those on foot to enjoy lovely romantic evenings of outdoor dining, drinking and shopping. Check out the event page for detailed event information and to peep some of this year’s participating vendors, including local favorites like Fellini Café Trattoria and Rye BYOB.

Girard Avenue Street Fest
May 6 (11:00 a.m. - 5:30 p.m.)
Hosted collectively by the Brewerytown, Sharswood, and Fairmount communities, this free, family-friendly events features 90+ local vendors and service providers, restaurants, games, live local music, and a special kids’ zone with bounce houses.  

South Street Fest 
May 6 (11:00 a.m. – 7:00 p.m.)
South Street’s biggest block party offers some good, old-fashioned family fun, food, and music. Stretching through Headhouse Square and along South Street, the event boasts a giant Maypole, a variety of live music performances, eating contests, a special kids’ zone, and, of course, Brauhaus Schmitz’s German-beer-and-dancing extravaganza. Stay tuned to the South Street Headhouse District’s site for more info on this year’s event.

Rittenhouse Row Spring Festival Saturday
May 6 (12:00 p.m. - 5 p.m.)
Philly’s most luxe street fest and a center city staple, the Rittenhouse Row Spring Festival features dozens of vendors offering food, fine art, beauty, fashion, as well as family-friendly fun, culinary demonstrations, and beer and cocktails booths lining Walnut Street.

Spring Brewfest at Washington Crossing
May 6 (12:30 p.m. - 4:30 p.m.)
Sample 100+ brews from dozens of local, regional and national breweries at Washington Crossing Historic Park. Top off the experience with food vendors, a souvenir tasting glass and live music à la bagpipe rock. Proceeds go toward supporting the park’s educational and historic programming.

Strawberry Month Kickoff Weekend at Peddler’s Village 
May 6-7 (11:00 a.m. – 5:00 p.m.)
Escape the city for a relaxing stroll through beautiful Peddler’s Village as it celebrates the start of Strawberry Month! This free-to-attend celebration features strawberry everything, so be sure to check it out if you’re a fan. Ice-creams, pies, lemonades…what have you. There will also be live entertainment and family activities from 11 a.m. - 5 p.m. through the weekend. Major strawberry fan who can’t make it this weekend? No worries! Each day in May, village restaurants will join the Strawberry Month fun by offering strawberry-themed food and drink specials, all month long!

Chestnut Hill Home and Garden Festival
May 7 (11:00 a.m. – 5:00 p.m.)
Philly’s Garden District hosts the annual home and garden themed festival which features 150 home design, garden décor, and hand-crafted furniture and accessory vendors. If you’re an HGTV addict like we are, this is the outdoor festival you certainly won’t want to miss!

Kensington Derby & Arts Festival
May 13 (12:00 p.m. - 6:00 p.m)
Join the Kensington and Fishtown neighborhood communities in a day of celebrating the arts, live music, great food, and catch the legendary parade of human-powered derby vehicles as they navigate a muddy, 3-mile obstacle course for the derby!

5th Annual Festival of the Peony
May 18-28 
Head to the 5th Annual Festival of the Peony over at Styer’s Peonies in Chadds Ford and frolic through peony fields and explore more than 30 varieties of peonies at this festival. A great opportunity to enjoy a peaceful moments in nature and snag some lovely photos of this beautiful flower that is a symbol of happiness and prosperity.

South 9th Street Italian Market
May 20-21
Long-famous for its cuisine, the South 9th Street Italian Market puts a spotlgiht on the well-loved staples that make this market so unique. Head to the Italian market May 20-21 to taste all the delicious samplings this neighborhood has to offer: homemade sausages, delicious cannoli, imported meats and cheeses, cappuccino, beef and poultry, and fresh pasta. Oh, and did we mention there's a greased-pole-climbing contest? You don't want to miss that!

Roxborough Spring Fest 
May 20 (12:00 p.m. – 6:00 p.m.)
Music, food trucks and craft brews...what more could you want from a festival? The Spring Festival at Roxborough features over 50 artists and crafters, local food trucks, delicious beverages for humans of all ages to enjoy, special kid-friendly activities, and a main stage for local performers fromt he Philadelphia area.

Fairmount Ave Arts Crawl
May 21 (12:00 p.m. - 4:00 p.m.)
This free-to-attend indoor-outdoor art festival takes over Fairmount Ave to showcase a wide range of local artists and performers. Restaurants, shops, bars and other businesses host painters, printmakers, photographers, sculptors and other multimedia artists, and there are lots of kid-friendly activities like face painting and crafts, so there is fun for the whole family.

Northern Liberties Night Market
May 25 (5:00 p.m.-10:00 p.m.)
Dozens of food and shopping vendors populate the bustling NoLibs corridor for an evening of delicious eats, shopping, performances through the evening. 

Night Tours at Eastern State Penitentiary
May 25 - September 4
The Eastern State Penitentary's Summer Twilight series combines the historic tours, exhibits and art installations that we know and love and offers additional hands-on activities, monthly themes and new events. Wind down with a brew at the Fair Chance Beer Garden on the penitentiary’s baseball diamond, offering craft brews from Triple Bottom Brewing Co.

Paddle Penn’s Landing
May 27 - September 4
It's finally here! Enjoy boat rentals and aquatic fun for the whole family. New this year: On select summer Saturdays, Paddle Penn’s Landing stays open late and offers nighttime Starlit Paddles, perfect for a little after-sun fun on the water, feeling the breeze.


We can't wait to check out all that our beautiful city of Philadelphia has to offer during festival month!

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Demetri Stakias is the founder of Real Estate Relief, and has been involved in Investment Realty since 2008.  Demetri has over a decade of experience in all facets of construction and renovation, has worked for years as an Accountant and Analyst for large organizations, and a specialization in solar and wind energy installations.

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