Top Things to Do in May in Pennsylvania 2023

Looking for things to do in Pennsylvania in May 2023? You can wave goodbye to those April showers and say hello to May flowers from food festivals to derbies and trout tournaments to music festivals across the state.

Food Festivals

1. Dining Under the Stars

people dining on main street
Dining Under the Stars

Every Wednesday through September, stroll, shop, and dine along Media’s State Street from Jackson to Orange when local restaurants and shops literally set up shop in the middle of the street during Dining Under the Stars. Closed to vehicular traffic, enjoy the warm summer breezes and a lovely dinner from your favorite restaurant in the heart of the downtown in May and all summer long.

When: May 3-Sept. 27
Where: Media
Cost: Free admittance

2. Penns Woods Winery’s Derby at the Vineyard

With big hats and bright colors, everyone is encouraged to dress to impress in their best Derby Day attire when attending Penns Woods Winery’s annual Derby at the Vineyard. Drink bottomless mimosas, check out the horse jumping competition, and enjoy live music and food vendors all day long. Even little ones can get in on the action with their Stickhorse Class for Kids!

When: May 20-21
Where: Chadds Ford
Cost: $15

3. The South 9th Street Italian Market Festival

people on street at Italian Market Festival
The South 9th Street Italian Market Festival | Credit: Kat Kuo

Enjoy fantastic food, live music, and shopping from local vendors during South Philadelphia’s South 9th Street Italian Market Festival — recently ranked as one of the “Best Specialty Food Festivals in the Country” by USA Today’s 10Best for 2023! If you’re up for a challenge, compete in the annual Grease Pole Climbing Competition and be sure to vote for your favorite cheesesteak vendor.

When: May 20-21
Where: Philadelphia
Cost: Free

4. Flickerfest at the Flickerwood Wine Cellars & Cocktail Lounge

artists performing at lounge
Flickerfest at the Flickerwood Wine Cellars & Cocktail Lounge

Celebrate Flickerwood Wine Cellar’s 23rd anniversary at their epic festival, Flickerfest! Kick off the festivities with "Name That Tune" on Friday night and keep the good vibes going into Saturday with live music, food trucks, and wine tastings. Don’t end the weekend without reflecting and relaxing at the Sunday morning yoga session.

When: May 26-28
Where: Kane
Cost: TBD

Art and Music Events

1. Lewisburg Celebration of the Arts

Immerse yourself in the arts with free exhibitions and workshops as downtown Lewisburg is transformed into a veritable art gallery during the annual Lewisburg Celebration of the Arts. This year’s theme is "Spring Beauty” with the incredible work of more than 100 juried artists on full display throughout the downtown. Even if art isn’t your thing, stroll through the celebration and enjoy the live music and foodie fun.

When: Now-May 13
Where: Lewisburg
Cost: Free

2. 15th Annual Wayne Art Center Plein Air Festival

a women painting by creek standing on Boulders
Annual Wayne Art Center Plein Air Festival

The 15th Annual Wayne Art Center Plein Air Festival offers a feast for the eyes as the newly painted works of 32 nationally recognized and emerging artists from throughout the U.S. are on display in the art center’s spacious and light-filled gallery. The festival’s focus is the beauty of Delaware Valley’s lush greens and vibrant spring colors painted by these highly talented artists outdoors (en plein air) in the spirit of the Impressionist masters, but in each artist’s own unique style.

When: May 13-June 24
Where: Wayne
Cost: Free

3. Millvale Music Festival

people walking around at millvale music festival
Millvale Music Festival

Put on your dancing shoes and get ready to get groovin’ at the Millvale Music Festival. Last year’s festival was voted “Best Music Fest of 2022” by Pittsburgh City Paper, and this year’s music extravaganza promises an even better time with more than 300 musical acts on 28 stages within a mile of each other later in May. Beyond the tunes, check out the comedians, 60 visual artists, food trucks, and games!

When: May 19-20
Where: Pittsburgh
Cost: Free

4. 84th Gettysburg Bluegrass Festival

people dancing on grass
Gettysburg Bluegrass Festival

Sway to the sweet sound of bluegrass melodies at the 84th Gettysburg Bluegrass Festival where the entire family is invited to enjoy yummy foods, lots of fun activities, local vendors, and live performances from Bluegrass’ long-time favorites to the industry’s latest newcomers. Want to hone your banjo, guitar, mandolin, fiddle, bass, or dobro pickin’ skills? Enroll in Jam Camp for four days of fun and instruction just prior to the festival.

When: May 18-21
Where: Gettysburg
Cost: Prices vary

5. Edinboro Art and Music Festival

A person playing a Banjo
Edinboro Art and Music Festival

The unique spirit of Appalachian culture and tradition is on full display during the annual Edinboro Art and Music Festival. Take in three days of festival fun with the art show gallery, hands-on workshops, and even special sing-a-longs for the kids. Join in a spontaneous jam session in town or check out one of the instrument workshops to spark a new talent. Before you leave, make sure to sample fare from Edinboro’s local cafés and eateries.

When: May 19-21
Where: Edinboro
Cost: Free

6. Harrisburg Artsfest

art piece made of bulbs and gauge
Harrisburg Artsfest

A must-do Memorial Day weekend tradition, the 55th annual Harrisburg Artsfest welcomes more than 150 juried artisans and craftspeople from across the country showing off their work in Riverfront Park. Bring the whole family to enjoy live entertainment, including Jazzfest, and family-friendly activities, along with nearly 30 food trucks.

When: May 27-29
Where: Harrisburg
Cost: Free

Outdoor Events

1. First Dam Releases of 2023 with Pocono Whitewater

Get the ultimate whitewater rafting experience in PA with Pocono Whitewater this May. During the First Dam Releases of 2023, the water from the dam release combines with the higher early springtime flows to make for some epic rapids on the Lehigh River. Strap on your helmet, grab your paddle, and take part in this classic May event in Pennsylvania.

When: May 13, 20, 27, 28
Where: Nesquehoning
Cost: $79.99 (ages 8 and up)

2. 33rd Annual Union Canal Days

people taking guided tours on boat
Annual Union Canal Days

Take a narrated boat tour through the oldest transportation tunnel left in the United States during the 33rd Annual Union Canal Days. History buffs will enjoy the importance of this Lebanon Valley historic treasure. Before heading home, enjoy the live music and be sure to visit the food trucks for some tasty treats.

When: May 20-21
Where: Lebanon
Cost: TBD

3. 2nd Annual Kinzua Cup Walleye Tournament

Get your fishing poles ready for the Willow Creek Sportsman’s Club’s 2nd Annual Kinzua Cup Walleye Tournament. The tournament was originally created to maintain and promote the beauty and available fishing opportunities of the Allegheny Reservoir. Sign up to participate, or simply sit back and enjoy watching fisherman compete to catch the largest fish, with prizes for the biggest catch.

When: May 20-21
Where: Willow Bay
Cost: Prices Vary

4. Kish Creek Trout Tournament

a person holding Trout fish caught
Kish Creek Trout Tournament

Get ready to reel in the big one at the largest tagged trout fishing tournament in Pennsylvania, the Kish Creek Trout Tournament. Started in 1994, the tournament is a great place for fishing enthusiasts to compete, mingle, and enjoy the Juniata River Valley in the peak of spring season. Anglers over 16 years of age, be sure to bring your valid PA State Fishing License.

When: May 20-21
Where: Reedsville
Cost: $35

5. Annual Farm Frolic at the Quiet Valley Living Historical Farm

A person holding a baby lamb in hands
Annual Farm Frolic

Join Quiet Valley Farm for two weekends of fun at their Annual Farm Frolic. Bring the whole family to experience this celebration of life with all the new baby farm animals. Watch baby chicks hatch from their eggs and hang out with the farm’s fuzzy baby bunnies and lambs.

When: May 20-21, 27-28
Where: Stroudsburg
Cost: $16 Adults; $8 for children ages 3-12 with advance ticket purchases; $18 Adults; $10 for children ages 3-12 at the gate; Free for children under 3 years of age

Other Events and Festivals

1. Festival of Fountains at Longwood Gardens

firework and lights at water fountain Longwood Gardens
Longwood Gardens | Credit: Daniel Traub

This year, be one of the first people to witness the new and improved, vibrant and illuminated fountain performances during Longwood’s Festival of Fountains. Starting May 11 Thursdays through Saturdays, take the whole family to enjoy a warm spring evening strolling through Longwoods’ ethereal gardens and secret pathways.

When: May 11-Sep. 24
Where: Kennett Square
Cost: Prices vary

2. 37th EQT Children's Theater Festival

a person in middle talking to kids and people around
37th EQT Children's Theater Festival

The 37th EQT Children's Theater Festival, in downtown Pittsburgh’s Cultural District, will keep the kiddos entertained for hours. This fun-packed event features live, top-quality professional theater performances from around the world, along with kids’ scavenger hunts and STEM and other fun activities throughout the three days.

When: May 19-21
Where: Pittsburgh
Cost: Free

3. New Hope PrideFest

people marching on bridge carrying Pride Flag
New Hope PrideFest

Get ready to let loose at the 2023 New Hope PrideFest! Celebrating its 20th anniversary, one of the festival’s major highlights is the grand parade that features more than 1,000 participants, local and national marching bands and floats, and New Hope’s 100 foot-long, eight-color Rainbow Equality Flag. Other fun events include the New Hope Pride Fair, outdoor music performances at PrideFest Live, and the Best Cocktail Contest where more than a dozen of the area’s finest try to craft the finest cocktail!

When: May 19-21
Where: New Hope
Cost: Free

4. Central Pennsylvania Fiber Festival

fiber wool in basket
Central Pennsylvania Fiber Festival

Explore the world of natural fibers and fiber arts at the Central Pennsylvania Fiber Festival. Held annually the weekend after Mother’s Day, you can shop the local vendors for handmade felted items, pottery, soaps, wooden fiber tools, and baskets. If you’re looking to get hands-on, take part in demonstrations of spinning, weaving, and soap making.

When: May 20-21
Where: Hughesville
Cost: Free

5. Greenberg Cadillac Museum

vintage Cadillac on display
Greenberg Cadillac Museum

See America’s largest collection of Cadillacs all in one place during the Greenberg Cadillac Museum. With more than 75 beautifully and lovingly restored Cadillacs made from 1903 to present day, the Greenberg Cadillac Museum houses 120 years of technology and style for visitors to enjoy. Rev your engines and get ready for this free event in Pennsylvania.

When: May 20-21
Where: Brookville
Cost: Free admission with donation

6. Portersville Steam Show

Get right into high gear visiting the Portersville Steam Show. The festival, called the Spring Gas-Up, has a wide variety of activities, including train and loom displays, craft building, tractor pulls, and a flea market, and features tons of tractors with gas engines, steam engines, and even pedal power.

When: May 20-21
Where: Portersville
Cost: Free

7. The National Road Festival

people riding on horses and horse carriage
The National Road Festival

Celebrate spring at The National Road Festival, the “world’s longest festival” stretching 300 miles along the Historic National Road. Celebrating the first federal road commissioned within the U.S., the annual festival features a mix of history, music, crafts, food, and fireworks. If you’re looking to transport yourself back in time, period clothing will be worn by many but is not required.

When: May 20-21
Where: Route 40
Cost: Free

8. The Great Pocono Raceway Airshow

Aerial view of Pocono Raceway
The Great Pocono Raceway Airshow

The Great Pocono Raceway Airshow returns Memorial Day weekend, headlined by the U.S. Navy's spectacular F-22 Raptor Demonstration Team, the famed Blue Angels. This stadium-style show features airplane acts and tricks by the Blue Angels for both shows on Saturday and Sunday.

When: May 27-28
Where: Long Pond
Cost: $25 for adults; $10 for kids 12 & under for advance ticket purchase

Looking for more fun activities in PA? Check out more events and festivals around the Keystone State. Follow us on Facebook, Twitter, and Instagram to stay up-to-date on even more great ideas and places to visit around our state. Don’t forget to never miss an update and sign up for our monthly Happy Thoughts e-newsletter.

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