A Long Weekend on the Eastern Shore
Crossing the Bay Bridge with three kids and a cooler: where we stayed, what we packed, and how to actually relax on a family trip.
The Eastern Shore is our reset button. Forty-five minutes over the Bay Bridge and the pace drops by half. Here is how we do a long weekend in St. Michaels with the whole crew and come home actually rested.
Where we stay
We rent a little cottage with a porch and a yard, every time. A pool is nice, but a porch with rocking chairs and a view of the water is what we actually use. Book early for summer, because the good ones go fast.
What I always pack
- A cooler with breakfast staples so mornings are slow, not rushed to a restaurant
- Bikes for everyone; the towns are flat and made for pedaling
- One nice outfit each for a proper dinner out
- Bug spray, because the marsh is beautiful and the mosquitoes are committed
The one rule
No itinerary. We pick exactly one thing per day (the maritime museum, a boat ride, crabs on a dock) and leave the rest open. The unplanned hours are the ones the kids remember.
Coming home
We always stop for produce at a roadside stand on the way back, and we always hit traffic at the bridge. I have made peace with both. The tomatoes are worth it, and the slow crawl home is a soft landing before Monday.
Some trips are about seeing everything. This one is about seeing each other. The Shore is just the backdrop.
