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Assateague Island in Maryland

Trip Overview

Canoe & Kayak Sailing Assateague

Solo canoe: Joel, Jeff, Jsaults, CWDH.

Tandem canoe: Patty/Theresa.

Kayak: Andy, Vic, Mike

Thursday, April 17 Sunday, April 20

A Thursday morning arrival saw Joel, Jim and I permitted for a 3 night stay at the best of the Assateague paddle-in sites, Pine Tree. Boats packed and a bit overpacked, despite our intention to paddle back to the launch the following morning to accompany the Friday arrivals into camp and grab the extra gear. Little did we know that CWDH was to take overpacking to a whole new level.

Heading out of the old ferry landing launch we paddled over into the wind shadow of Great Egging Island and raised sails. And that was that for paddling as we sailed effortlessly down Chincoteague Bay to our site.

A dawdling day in camp, with bayside shoreline progging, beach hikes and general laziness lead into a dusk paddle to light a cyalume marker on a peninsula point as CWDHs night time guide. Back acamp midnight rolled around, followed by 1am, but still no CWDH. Up at 4am, to bed at 1:30 Im sure glad we didnt tire ourselves out by paddling in.

Friday morn we paddled into a slight breeze back to the old ferry to find Patty and Theresa already loaded, meaning gear-in-boat, not the more typical Squatter connotation. Vic and Andy too, both trying to figure out how to stuff a large volume of gear in to a small volume of sea kayak. With the Eagles entrance Jeff arrived and our party was complete, except for the still missing CWDH.

Joel suggested that he must have put in at Chincoteague instead and we agreed that that was likely. Or that he had once again missed the Pine Tree site and night paddled down to Green Run. Or Pope Bay. Or Virginia Beach. One just never knows with CWDH.

The wind having picked up agreeably a second canoe and kayak sailing regatta breezed us down to Pine Tree, which was now quite unlike the near deserted site we had departed a few hours before. A gorgeous weather weekend had drawn paddle in campers from far and wide, and every Assateague backcountry site was book to capacity.

Capacity and then some. One unpermitted late arrival approached me and asked if I thought anyone would mind if he camped for the night, prefacing his query with the words, "Are you nominally in charge of these people?"

Nominally in charge? Not even on my best day of Duckhead living.

A cross island bocce game was cut short when we ran out of beer on the 5th hole, despite carrying a backpack cooler. Strolling down to the landing to eye the collection of craft a curious vessel caught my attention; a cargo vessel in dire need of Plimsoll Lines was approaching. A canoe with gear piled into towering mountains both fore and aft that the lone paddler needed a periscope to see ahead. A canoe containing all and ever manner of gear and supplies, including a Webber grill, cast iron cookwear, 16-piece carving knife set, bags of spuds and a half a pig in bacon and sausage. And a 16 lb turkey*.

It could only be CWDH. (*Ill let him describe how not to thaw a frozen turkey on the dashboard of a Ford van.) Eyeing the Malecites sheer freight tonnage Joel, Jeff and I decided the time was ripe for a dusk paddle and hurried for our boats.

Heading up the long Pine Tree gut to the south I was pondering the advisability of describing the waters unusual depth and bottom contours to my companions when Jeffs pole plunged suddenly off the sand bottomed shelf and into deep water muck. No Duckhead trip is complete without a swim or aggressive stepout and this was one of the better of the latter. The water filled boats pile driver effect as Jeff attempted to raise and empty it was an iconic moment. Well photographed too Joel.

Jeff decided that what was needed was undoubtedly more beer and we headed back to see if CWDHs Sherpas had succeeded in moving the mountain. Yes, and yes there was more beer.

Saturdays forecast predicted the wind shifting to the south and a day paddle was undertaken to the long abandoned Jims Gut site, culminating, of course, in an effortless sail back to camp. Feet on the rudder pedals, moving right along in the Sea Wimp under full sail and looking to see Jim, Jeff, Joel and Andy all sailing along beside me was a wondrous sight.

Sailing the Wimp it occurred to me that one benefit of wind cruising is the ability to do minor housekeeping while still making time and maintaining course; get a beverage, light my pipe, maybe take a photograph or write a few notes.

Saturdays night float evolved from a sunset photoshoot and evolved into a long fireside sip and sit. No last man standing for me tonight as I left Joel and CWDH solving the worlds problems in the wee hours.

Despite the late and later nights around the fire camp was awake early. Jim departed on a solo sail back, soon followed by Jeff, Joel, Andy and I, all again under sail.

The wind on this last sail was blowing harder and began to turn to the east, presenting more challenging conditions, but we were all now better practiced and confident of our abilities.

Confident. Overconfident. Whatever. Fortunately I was able to careen ashore at Great Egging Island, my last chance at stopping to unstep the sail before I blew ashore somewhere on the Jersey coast.

Packed, racked and en route home before the front moved in, wondering how the paddle out was for Theresa, Patty, Vic and CWDH.

More Photos

Joels Photos:

Andys photos:

Jims Photos:


Backcountry sites have chemical toilets, picnic tables and fire rings. NOTE: No potable water is avaailable in the Assateague backcountry; pack in all drinking water that you will need.


Canoe & kayaks with sails


Minimal Nat'l Seashore entry fee and backcountry permit fee.


Rte 50 to Rter 611 east to the Atlantic Ocean


Park handout maps of the backcountry areas are available.

  • Duration: 2-3 Day Trip
  • Skill Level: Intermediate
  • Water Type: Open Water/Ocean
  • Group Rates: No

Locations on this Trip