Family Fun at the Gulfport Artwalk and Trolley Ride

Family Day is sometimes Family Night for this family. We usually have family adventures on Saturday mornings, but on the first Friday (or third Saturday) night of the month we like make our way to Gulfport for some free family fun, which is what we did on May 3rd.

The city’s best street, Beach Boulevard, is lined with artists showing off their metal sculptures, painted driftwood, photography, collapsible wooden baskets, handmade jewelry and many other kinds of art, as well as a few food vendors. It’s almost like the night version of the Gulfport Tuesday Fresh Market.

Plus all the restaurants and shops stay open late and often feature live music on these nights. Though, I must say there’s a woman at one of the restaurants who likes to belt out old songs way off-key. I prefer to listen the young jazz band play outside of Pia’s Trattoria.

There are several places to eat on Gulfport Beach, like Tangelo’s, Pia’s, Peg’s Cantina, O’Maddy’s and Backfin Blue Cafe, but we’re usually working with a tight budget and picky palates on family outings, so we went to Yummy’s (2914 Beach Blvd S). It’s a hot dog joint that also serves sandwiches and shakes. I actually had my first Chicago style hot dog on this visit.

It was good, but one hot dog and a puny portion of less than stellar potato salad did not satisfy this girl, nor her husband. So we split an Italian Beef Sandwich, which was like a Philly cheesesteak without the cheese with a side of au jus (typically served with a French Dip Sandwich). It definitely hit the spot; it filled us up and was delightfully beefy, juicy and toasty.

Yummy’s has a bunch of different hot dogs to choose from. Just plan on getting at least two dogs and expect a poppy-seed bun. This is their standard hot dog bun, but you can request a plain one, which is what I get for my boys. They also have lots of hand dipped ice cream and milkshakes to choose from.

Besides markets, art and hot dogs, Gulfport is also known for its unique characters. I’ve seen someone walking around with an iguana on their shoulder (like it was an everyday occurrence) and another on stilts. This time while we were eating our hot dogs, we were approached by a friendly female pirate. She talked with a salty, British accent and invited us to the pirate festival at John’s Pass happening the following weekend. My son was very excited about our visitor and would’ve talked to her all night long, but we had a trolley to catch!

The trolley is my boys’ favorite thing to do in Gulfport. You can ride for free every Friday and Saturday night from 6pm-10pm. However, the artwalk (also free) is only on the first Friday and the 3rd Saturday of every month. You can park at the Gulfport Library (the easiest place to find a spot on a busy weekend) or anywhere on Gulfport Beach (just get there early). You can wait at one of the stops, but we usually just walk towards the beach and flag the trolley down when we see it. To get off, just pull the rope and a little bell will alert the driver. The trolley drives all over the beach and as far north as Fazio’s Pizza on 15th Avenue South.

The trolley is really a bus but it has the nice open windows and wooden benches so it feels like a real trolley. The seats are comfy enough and it’s never too full. The boys love to hang their heads out and take in the people and the scenery. They love riding it so much, we could probably stay on it for an hour and skip the artwalk and dinner, but I like a little variety on Family Night.

This was our third time doing the Gulfport Artwalk and Trolley Ride this year and we’ll probably do this again a few more times. I love that it’s very budget and family-friendly, features art and you can meet lots of interesting people. You can check out the next Gulfport Artwalk and take a ride on the Gulfport Trolley this Saturday, May 18th. Bring the kids and grandparents with you! It’s fun for all ages!