your paddlesports destination

Deer Island in Maine

Trip Overview

October is not a traditional time to go paddling in Maine. The winds are stronger, the weather unpredictable, and the nights start getting genuinely cold. The advantage is, however, that you pretty much have the place to yourself, sharing it only with the occasional lobsterman. We decided to paddle amongst the archipelago of islands south of Stonington, ME, located on Deer Island. After her 1,200 miles solo kayaking expedition from New York City to Tabusintac, New Brunswick, my wife was also ready to get back into a kayak. We've been Maine Island Trail Association (MITA) members for two years in anticipation of making time to do this trip, and this was our first opportunity. Although the weather outlook was average to poor, we figured we could make it work. The MITA trail is simply phenomenal, and their guidebook is very well done. You are never left guessing exactly where the islands and campsites are, or how best to approach them, or what conditions are like on each island on the trail. In order to use the islands, many of which are privately owned, you need to be a MITA member, so it's well worth joining.

We arrived at Old Quarry Ocean Adventures, the main outfitter in the area on a Thursday night and checked in with the owner, Bill to get a campsite and arrange for launching and parking our car during the trip. Old Quarry is actually located right next to a large granite quarry and shares a protected cove with a lobster fleet. The campground itself is immaculately maintained and well-appointed with bathrooms, launch ramps, and trailer hookups (for those that roll that way). There were a few other campers there, mostly bikers touring the area.

We got our tent set up on a platform after making plans to see Bill in the morning to launch and set off to find some food. Stonington has a Main Street with three restaurants on it. You can pretty much pick any one of the three and be set. We settled on the Harbor Cafe (which isn't bad). As soon as we got back and in the tent a deluge let loose and continued throughout the night, dumping several inches of rain. Thankfully we had invested in a top-flight 4-season North Face tent a few trips ago, so we stayed nicely dry.

The next morning we got breakfast at the Harbor Cafe and filed our float plan with Bill before driving over to the granite slab launch ramp on the property, loading our kayaks, and donning our dry suits (the water was at around 40 degrees F). Forecasts called for winds in the 20 knot range for the day, followed by 15-20 knot winds with gust up to 25 the next day, followed by a storm the day after that. With the extensive protection provided by the often tightly-packed islands, we figured we could stay in the lee of something almost the entire time and pushed out of the cove.

If you love kayaking, then you know about Maine and probably have a well-defined image of what it's supposed to look like. It looks exactly like it should. Craggy, rocky islands crowned with sparse trees, paved with irregular masses of moss-enveloped rocks punch up from the ocean and are enveloped in fog. The lowing of fog horns is constant and the high tides (in the 12-13 foot range while we were there) constantly alter the landscape and vary the conditions. As we exited the protected cove we came into more open water where the wind had stirred things up, but due to the protection of the islands, we were able to make quick dashes from island to island.

Waves were in the 2-3 foot range between the islands and 4-5 feet in unprotected areas, but the fact that we were never too far from an island where we could land made it feel very manageable. We began paddling around the islands and took a brief tour of the area to see what that speed of wind would do to the water for future reference and then went to Green Island, where Bill had told us that there was a beautiful water-filled rock quarry. After doing some zigging and zagging to avoid the worst of the waves, we pulled into a quiet cove and took the short walk to the quarry, which makes a great swimming hole in the summer, I'm sure.

After relaxing a bit, we decided to head out and make camp of Steve's Island, a small, rocky islet across from the Merchant Row islands north of Isle a Haut. The wind had picked up even more at this point, but we made our way directly into it and splashed our way to the island, where we looked for a good landing spot. After seeing one or two mediocre ones, we paddled around the southern side of the island and were immediately caught up in 4-5 foot reflecting waves, prompting us to land in the nearest cove. This snap judgment robbed us of the time to take a close look at what the shore would look like at low tide (it was nearly high at the time we landed). Although it ended up that there was a sandy shore that extended about 20 feet from the island proper, there was another 20 feet of seaweed-covered, slippery rocks that would make launching a pain at low tide. Nonetheless, we got the kayaks up onto the island's shelf and set up camp, putting on warm clothes and walking around the very limited, but beautiful acreage. As the tide receded, much of the island was revealed, giving us more to explore.

The forecast for the next day called for rain and winds in the 15-20 knot range with gusts to 25 knots. We decided to do a paddle to Sellers Island, a postage-stamp with a sand beach across the Eggemoggin Reach from Deer Island. Our launch was greeted with a driving rain and fog, but this did little to reduce the beauty of the paddle; the islands enshrouded in fog combined with the dulling of sounds made it feel other-worldly. Our paddle took us through the Deer Island Thorofare, which kept us on the lookout for lobster boats, but we only saw one or two the entire paddle. As we came around Stinson Neck the wind picked up significantly and just kept blowing harder and harder. Lobster boats were motoring into East Side Cove or anchored in the lee of some of the near islands.

As we began to push across the reach conditions deteriorated rapidly with the wind rising in pitch and the waves getting larger, quickly progressing from 3 foot breakers to 4-5 foot breakers. Half a mile into our crossing, we realized that conditions weren't just bad and stable, they were bad and getting worse, so we sweep stroked and braced furiously to get our fully-loaded kayaks turned around and then began a difficult progress in a following sea towards shore where we could get in the lee of Sheep Island. The waves were too steep and close together to surf and at one point (I'm not sure how) I was looking almost straight up at the sky a closely packed set of large waves (probably wake-enhanced) gripped the stern of my boat and suck it straight down. I was dumped almost on my side and ended up bracing hard by holding my Greenland paddle (my now favorite Feathercraft Klatwa) on one end and bracing off almost the entire length of the paddle, which allowed me to get upright. I'm pretty sure I would have capsized with a euro paddle.

With the weather making up our minds for us, my wife made the call to push to Campbell Island, a large island protected deeper in the Reach and nestled in Greenlaw Cove. Calm enveloped us as we slid towards the island, protected by the line of islands blocking the wind coming from the NNW. After examining the island we chose the better of the two landings as the cold rain re-emerged and a large fog bank obscured anything further than 200 meters away.

Campbell Island looks like the ideal setting for a scene from "The Lord of the Rings". Moss drips from tall, scraggly evergreens shallowly anchored in the thin soil, which is carpeted by thick green moss. The island was the site of a late nineteenth century archeological dig that found an European in full armor and the burial site of a Native Chief, and it is stunning. We wore that word out as we hike the 2 mile long trail that runs around the island. One of the most fascinating aspects of Campbell is that from one footstep to the next you can encounter completely different environs, which range from the aforementioned evergreens to lush fields of ferns, to salt marsh. The chirping of curious red squirrels was constant and an addition to a menagerie of birds, my wife also spotted a small doe. As night fell the rain and wind increased markedly with the forecast calling for 30 knot winds the next day.

Upon waking we found the rain falling in sheets and the wind meeting and exceeding the forecast, meaning that we would spend the day in the tent relaxing and planning the next day's paddle. With the forecast being for one nice day followed by very high winds, we decided to make the most of the opening the next day and planned on essentially circumnavigating Deer Island and Little Deer Island by paddling NW up the Eggemoggin Reach and then Paddling S down the East Penobscot Bay, ending up just short of our original launch point at tiny Weir Island.

The next day was calm and cloudy and we quickly donned our dry suits and pushed up the Reach towards the Deer Island Bridge, enjoying beautiful vistas and large colonies of seals that followed us for miles, but were highly skilled at avoiding being photographed by diving. As we came around the northern point of Little Deer Island we were treated to the spectacular view of cloud-shrouded mountains and rugged islands that typifies the Bay. The water was relatively calm with some ocean swell present at the lower reaches of the Bay.

We paddled past gorgeous island after gorgeous island with the area around Pickering Island being the most incredible. After around 25 miles we made it Weir Island, which turned out to a steep, rocky ledge with some trees growing on it. After trying several approaches we finally found a spot where we could sneak onto a sandy beach through the surging water by using our hands to push the kayaks from rock to rock before we got dashed against them. Weir was small, but beautiful and we were lulled to sleep by the fog horn on nearby Mark Island.

The next morning we checked the forecast and found it still called for winds that would make paddling less than fun, so we paddled back to our launch point and loaded up to head back south for warmer, calmer climes.

A few notes...
Cold water protection is an absolute necessity for Maine. We wore our drysuits with warming layers underneath; the water was numbing to the touch. Having a VHF radio in this area is a must. Not only does it provide you with the weather, but with the large amount of commercial fishing traffic, it gives you communication with the principal users of the waterways in the area.

You can see more pictures and download the GPS files for the trip at our website at


we stayed at the campground run by, parked at, and launched at Old Quarry Ocean Adventures


NDK Explorer and CD Cypress


MITA membership to stay on islands on the MITA trail.
Parking and launching from Old Quarry.


The address for Old Quarry won't lead you all the way to the main building. The following grid will:
4410'20.89"N 6838'22.18"W.
This is an improved dirt road, but it's pretty bumpy, so if you don't have 4WD, go slowly.


Waterproof charts of the area are key since navigation can be confusing with all the islands. Waterproof Chart #104 covers the area, or utilize NOAA 13313, 13316 and 13318 to get the same coverage.
  • Duration: Extended Trip
  • Skill Level: Intermediate
  • Water Type: Open Water/Ocean
  • Group Rates: No

Locations on this Trip