As an adult, we used to make an annual trip to Crisfield MD and stay for 4 days at the State Campground.
Janes Island State Park.
http://www.dnr.state.md.us/publiclands/eastern/janesisland.asp
We’ve been making 4 or 5 day family trips to Janes Island, usually in March or early April. Some trips we’ve ended up in flip flops and shorts, some trips we’ve been snowed on.
The park is closed to camping then, but the 4 rental cabins are open year round. The off-season cabin rentals are a delight, especially when coming back from a long daypaddle explore in the wind and cold. The empty park is another peculiar delight
Even empty the tent/trailer campsites seem pretty dense-packed, with little understory screening them. Boating at Janes seems set up to accommodate motor boaters, with expansive piers and slips on both the mainland and the island. The marinas in nearby Crisfield must house thousands of boats. I’ve never seen it in-season, but the locale looks to be mighty busy in summer.
Off-season Janes Island makes for a fine paddler park, with 30 miles of marked trails through the marshes and around the Tangier Sound side of the island. During most of our peregrinations there, both in the marsh and on the Sound side, we’ve had little boat traffic, and the sandy island beaches are invitingly empty.
There is also a diversity of paddling a reasonable drive away. If you have two vehicles to set a shuttle - or dare to time the tides far up a narrow tributary - there are upland creeks and rivers nearby (Manokin, Kings Creek, Monie Creek, Murmasco near the mouth of the Pocomoke). As an added bonus many eastern shore shuttles are 3-turns quick and simple.
My brother and I are always talking about getting back down to the Assateaque area for a long weekend. I will have to share your trip with him. I get the feeling from articles and trip reports here that there is alot of potential paddling along the Eastern Shore.
If you are interested in eastern shore paddling Ed Gertler’s “Maryland and Delaware Canoe Trails” is a must. His guidebook format, mentored via Roger Corbett (there is a good story there) is hands down the most user friendly I’ve seen, and has been adopted by other paddling guides.
Gertler’s eastern shore section lists 33 rivers and creeks, not counting the chapters that include other ocean drainages (Christina River, Delaware Bay and Atlantic Ocean), which add another couple dozen routes. And also not counting hundreds of smaller creeks and tributaries off the main waters too obscure to include in a guidebook
At one point I counted something like 54 different rivers, creeks, bays and tributaries I’ve paddled at least once on the Delmarva, and I’ve only done half of the ones in the Gertler guide.
From almost any point on the eastern shore a few of those creeks and rivers are typically within a half hour’s drive. Combine those mostly protected routes with the unending choices in open water bay or ocean paddling for sea kayakers and eastern shore is close to paddling paradise.