A weekend in Port Washington

We’re on a mission—to explore towns, places, and activities around us in Milwaukee. Enter: a fun weekend in the charming city of Port Washington, Wisconsin.

Here’s how to spend a weekend in Port Washington.

About Port Washington

Port Washington, Wisconsin, is a charming harbor town perched along the western shore of Lake Michigan, just 30 minutes north of Milwaukee. Even though it’s close in distance, Port Washington has its own unique flavor and distinct brand of lake-life charm. With a population of around 12,000, it blends small-town friendliness with a distinctly coastal feel—often compared to a slice of New England in the Midwest.

Founded in the 1830s, Port Washington grew around commercial fishing, shipping, and the natural deep-water harbor that continues to define its identity today. Its historic downtown is filled with 19th-century architecture, locally owned shops, and incredible waterfront views.

Port Washington is known for its lighthouses, scenic shoreline paths, thriving marina, access to the Ozaukee Interurban Trail, and a walkable downtown full of boutiques, pubs, and cafés.

During our late fall-time visit, the town gave us a charming respite from the city, punctuated by crisp (okay, chilly!) breezes off the lake, incredible views, and a soundtrack of waves lapping against harbor walls.

A chilly weekend in Port Washington

With Lake Michigan shimmering alongside its historic harbor and crisping leaves in the background, Port Washington is a perfect fall and winter weekend escape just north of Milwaukee. This lakeside town charms with its blend of maritime heritage, downtown boutique shopping, and welcoming local flavors.

Here’s how to make the most of a cozy weekend in this harbor town.

Port Hotel

Check into the elegant Port Hotel, a beautifully restored 1902 neoclassical-style lodging offering suites with fireplaces, high ceilings, and downtown views. The historic ambiance—creamy brick exterior, vintage charm—and modern comforts make it a warm, inviting base for exploring Port in the fall.

We loved our stay at the Port Hotel, especially the four-post bed, fireplace (I couldn’t get enough), and in-room jacuzzi. Another huge highlight was walkability: we parked our car at the hotel and walked everywhere. The downtown and lakefront are just blocks away; food, shops, and local haunts are well within reach.

Explore downtown

Downtown Port Washington is full of small town ambiance, and is lined with local businesses.

We checked out:

• Candid Form Boutique had modern, quirky, and beautifully curated clothing, knick-knacks, and accessories, and I loved every inch of their collection.
• The Purple Turtle Artisan Collective was stocked with handmade goods and art.
• Sherpers is a multi-generational outdoor store with a back room full of vintage goodies.
• Fifth-Main was a stylish consignment shop for both men and women’s clothes and accessories.

There’s something for everyone, with more shops and stores to peruse, enjoy, and support.

Historical sites

There’s also a historical side of Port Washington that’s waiting to be explored. There are striking churches perched above downtown (the staircases provide a great workout, with an incredible view as a reward), along with preserved historic sites littered throughout town. We loved reading the plaques about local maritime history, and following a scenic path down to the lakefront.

Key historical sites:

• Port Washington Lighthouse and Light Station Museum. A beautifully restored 1860 light station, keeper’s quarters, and an iconic 1935 art deco lighthouse with stunning harbor views
• Judge Eghart House. A preserved Victorian home, built 1872, that offers insight into late 19th-century family life in the Port Washington area
• Downtown Historic District. A self-guided walking tour that highlights Italianate, Queen Anne, and Federal-style buildings, including the Old Firehouse (1928) and the stunning St. Mary’s Church (1882)
• Port Washington Historical Society Resource Center. Located in an 1852 building, the seasonally open center is home to changing exhibits and local history collections
• St. Mary’s Church. A Neo-Gothic masterpiece built in the 1880s, this church has incredible architecture, with an outdoor staircase that leads to one of the best views of town
• Old Firehouse. A 1928 Mediterranean Revival style building with a distinctive hose tower

Harbor

No trip to Port Washington is complete without a walk along the harbor and out toward the lighthouse. In fall and winter, expect wind—strong, chilly, and invigorating—with waves that sometimes crash dramatically against the breakwater.

Bundle up, take your time, and savor the fresh air and views of Lake Michigan and the iconic red-roofed lighthouse standing at attention at the end of the pier.

Food and drink

Here are a few recommendations of Port Washington spots for food and drink.

• Daily Baking Company. An aesthetic stop for coffee and pastries
• Sir James Pub. Keep an eye out for the unofficial “captain” of the pub—a local legend who stands guard over the ship-shaped bar and adds to the quirky charm
• Inventors Brewpub. They have great beer and a delicious Friday fish fry!
• Moonlight Tavern. This old school supper club is attached to the Port Hotel, and it was both delicious and convenient!
• Cavalier Wine Bar. We enjoyed a delicious wine flight, which included zero-proof options with traditional whites, reds, and roses. Highly recommend!

Port Washington’s charm lies in its simplicity: cozy stays, walkable streets, waterfront vistas, and a small-town feel rich with history and local flavor. For a fall weekend filled with crisp air, good food, and lakeside adventure, this harbor town offers a getaway that feels both refreshing and deeply comforting.

Worth a visit

Overall, Port Washington was a wonderful destination for a weekend getaway, filling our itinerary with charm, walkable streets, rich history, and Lake Michigan scenery.

We loved the quaint, waterfront vistas, and the relaxing respite of a weekend away (that was still close to home). If you’re looking for a Midwest town worth visiting, be sure to prioritize Port Washington.

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