Venetian Weekend in Port Washington
Summer fun for the entire family on Labor Day Weekend
Port Washington, a charming lakeside town, is a rare gem of a destination that balances kid-friendly excitement with a bona fide vacation experience for adults. Just 30 minutes drive north of Milwaukee and less than 2 hours from Chicago, Port Washington holds onto its rich history as a Lake Michigan harbor town.
This weekend getaway was a captivating blend of outdoor adventures and relaxation, from a bustling farmers market and playful playgrounds to serene beach strolls and great food for every taste. Port, as the locals call it, is a truly special weekend destination that checks all the right boxes for kids and adults alike.
Day 1: Shopping and Strolling downtown Port
The approach into Port, with Lake Michigan coming into view and a happy mural welcoming us, set the perfect tone for our getaway. We were truly looking forward to this Labor Day weekend trip as we arrived after an easy drive up from busy Chicago.
Our adventure began with a visit to the Saturday Morning Market which was conveniently located in front of The Port Hotel. This locavore’s market is open from 8:30am - 12:30pm on Saturdays, June thru October. Our little one, Sully, couldn't resist the blackberries and he finished the entire container before we left the market (we shared a chuckle with the vendor as I returned the empty container back to her). We also picked up coffee, donuts, cheese curds, goat soap, and honey. With our market goodies in tow, we decided to snack at Dockside Deli, enjoying the public spaces downtown by the marina.
While at Dockside Deli, we ordered sandwiches to-go, and I'd highly recommend the Harbor master and the Tuna melt. Afterward, we explored Sherpers, a legit outdoor and camping store with an impressive selection. Sherpers also rents Oru kayaks if you’re looking to get on the water! Duluth Trading is right next door and offers a wide range of their high quality workwear and outdoor clothing. Fun fact: This store was just Duluth’s second location (they now have over 60 stores). We picked up a new hat for our kiddo before heading out!
We chose North Beach Park for our picnic lunch and opted to walk the 0.8 miles uphill. You can also drive or bike this route depending on your abilities and ambition. On the way up we were surprised to find a 1.8 mile single-track mountain bike trail and wooden features tucked away at the bottom of the hill, just north of Guenther Park.
Bringing a Fat Bike? Port Washington’s two beaches are also open to fat tire bikes!
Our next stop was the family-friendly Possibility Playground, a bustling place that accommodates kids of all abilities. This park has ample parking, picnic spots and is just steps away from incredible views of Lake Michigan overlooking the North Beach. Port's Beer Garden was a delightful find and on this Saturday they had live music! We enjoyed some cider and water all while being just a short walk from the playground.
Back down the hill, a lakefront path takes you to the Breakwater Light which offers panoramic views of the marina. The network of paths, signage and Port Washington's public restrooms and rest stops make this town incredibly walkable. We continued over to Frankies Ice Cream, a local gem that serves up ice cream during the summer months from a converted Airstream RV.
While we waited, we ran into a local photographer, Marie Herian, who snapped this awesome photo of us!
Our evening wrapped up with a to-go order from John’s Pizzaria with some favorites for our 1.5 year old; pepperoni and spaghetti. We brought this back to our room at the Port Hotel; a historic inn with modern amenities (and a friendly innkeeper to boot!). You can nearly hear the stories of past travelers as you walk the halls; the current building dates to 1902 and this plot of land has been home to a hotel since 1857. The room accommodated all the chaos and equipment that a toddler brings, and the availability of 24-hour gas stations came in handy during an unexpected late-night run for baby Tylenol.
Day 2: Cardboard Regatta and Boat Parade
Banjole Brews was a pleasant surprise with guitars and ukuleles to strum while waiting for our chai and mocha. We also sampled a blueberry scone and fig bar. Daily Baking is another great breakfast spot if you’re looking for a more substantial breakfast; we ordered the quiche and avocado toast.
Venetian Fest kicked off at noon in Rotary Park, starting with a free kids obstacle course. We also tried our hand at bean bag golf and set the course record (we were the first to do it ;). For lunch we opted for a Polish sausage with all the Chicago-style fixin’s from a street cart, a quintessential summer experience. We chatted with Fred Pugh, the owner of One Of A Kind, who was also a nursing home caregiver.
The main attraction after lunch was the Cardboard boat regatta. The competition started with laughs as the MC played the Titanic theme song while teams readied their vessels. The cardboard boats were impressive, some sturdy and others hilariously unfit for the water. This was certainly the highlight of the weekend and we cheered and laughed alongside hundreds of other spectators.
For Dinner, Tellos is another delicious and kid-friendly option. They delivered traditional Mexican food and a shaded outdoor seating area. Try the quesadilla and the Wisconsin Style Burrito with a corona. Follow this up with chocolate ice cream from The Chocolate Chisel (because, why not), which offers an excellent selection beyond just ice cream. We had time to kill before Venetian fest so we walked over to the sandy shores of North Beach. This is the perfect spot for a swim or to watch locals chasing the afternoon surf.
As evening fell, Venetian Fest’s Lighted Boat Parade took center stage. A band played as the sun set, and boats circled the harbor with their lights, creating a "4th of July" atmosphere as a bookend to Summer. This is a truly special experience and our little one was captivated, pointing and clapping as the boats went by.
Day 3: Sunrise
The next morning, we savored the sunrise with fishermen and sun catchers. It was the perfect ending to a fantastic weekend. Our getaway to Port Washington was a delightful blend of outdoor adventures, delicious food, and relaxing moments.
It is rare to be so close to home and feel like you’ve had a true vacation; Port Washington gave us just that. Port’s Venetian Fest on Labor Day weekend is the type of experience that leaves you checking the Zillow listings as you drive back home.
