You can always tell those who have explored the bay side of the peninsula first and then backtracked through Sturgeon Bay  to come back up this side. Generally, these are the ones who race right through Jacksonport as if they didn’t know it was there and then turn around to try to find what they missed.
At one time, Jacksonport rivaled Fish Creek  as epicenter of economic booms on Door County . Once the local lumber was depleted, Jacksonport’s docks were relegated to fishing boats. The last community to be settled in the county, Jacksonport caught one of the Germanic immigrant waves, and its annual Maifest (www.jacksonport.org/maifest ) is among the larger shindigs held throughout the summer.
Somnolent Jacksonport today sports a few antique shops and gift cottages selling wares and crafts from dozens of Door County artists. A lazy strand of sand acts as a beach, and top-notch fun comes in the form of the sweets at the Town Hall Bakery (6225 WI 57, 920/823-2116).
Right downtown is the pinnacle of Jacksonport’s developmental ambition: the Square Rigger Lodge and Cottages (6332 WI 57, 920/823-2404, www.squareriggerlodge.com , from $80/100 s/d). More than a dozen basic but comfortable modern motel/condo units overlook the water (some do not), and most have private balconies or patios. One- to three-bedroom cottages also line the waterfront. They have lively fish boils here nightly in July and August, and four times a week in the off-season.
The supper club of choice is Mr. G’s (5890 WI 57, 920/823-2899, lunch and dinner daily, $6–14), with a ballroom that has in the past had live entertainment, though most entertainment today comes from tall tales at the joint’s Tiki Bar, part of the local bars’ Yacht Club, which is more Jimmy Buffett than America’s Cup to be sure.
If that’s too sedate, you may also have time for a margarita and some homemade salsa at J.J.’s (6301 WI 57, 920/823-2700) nearby!