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Five Epic MA Paddling Trips to Earn Your Stripes

Posted by on June 12, 2012

People always give me strange looks when I provide my candid answer to the seemingly obvious (or maybe not so) question “where has your most epic paddling been?” Answer: Coastal Massachusetts. It’s true that I’ve paddled in some pretty amazing places from the kayaking Mecca of Downeast Maine to the wildly gorgeous coasts of Kenai Alaska. However, it’s also true that I haven’t had to travel to the ends of the world to test my paddling skills. There are plenty of challenges right here in my own backyard that have helped me earn my stripes. The following is a list of five local challenges in increasing order of difficulty:

1) The Graves

The Graves is a desolate pile of rocks located roughly 12 miles east of Boston’s Inner Harbor. The name alone is as imposing as the trip to get out there. The trip involves crossing either of the busiest shipping lanes in Boston Harbor and then putting the outermost of the Boston Harbor Islands over 2 miles to your stern. It’s pretty hard to be more isolated and within view of a major metropolitan city! Once you’re there you’ll be in for an epic surf session as average ground swell turns this labyrinth of rocks into a sea kayaker’s dream playground!

This is the most accessible of the “Epic MA Trips” and a solid trip plan is presented in the Boston Harbor Lighthouse Tour Trip Report. Expect the sea conditions to build even on an “average” day when you pass by the Brewster Islands and take care not to get caught too tired out there as you’ll be fighting a SW wind on the return trip! Also, cell phones don’t work that far out so make sure to have a marine VHF in the group. Lobster boats and sports fishermen frequent this area so help is never too far away despite the isolation.

2) MV Crossing from Woods Hole

The open water crossing to the island of Martha’s Vineyard from Woods Hole offers a true test in kayak navigation. The tidal currents that exist in Martha’s Vineyard Sound are some of the strongest in all of MA (reaching 3.5 knots at mean tide). The crossing itself is only 4miles but you must take care to factor in the current with an aggressive course correction to ensure that you meet the island and are not swept right by it. Once you get out there you’ll be rewarded with a relaxing few hours on the beach, exploring quaint villages, or otherwise taking in the island life. Check out the MV Crossing Trip Report for more details.

This trip is best attempted on weekdays when the traffic in Martha’s Vineyard Sound is less heavy. Watch out for boat traffic, especially ferries and sailboats, as the crossing takes you through a busy and wide channel that services the island. Also, make sure to have a contingency plan in the form of an island layover or ferry ride back in the case that afternoon conditions on the Sound deteriorate (this is fairly common).

3) Circumnavigation of Cape Ann

The circumnavigation of Cape Ann is a marathon-distance epic that has become popularized by the annual Blackburn Challenge Race. The trip is typically done clockwise starting from Gloucester High School, heading North on the Annisquam River, and following the rocky coastline for 20+ miles for a landing in Gloucester Harbor. Expect varied conditions ranging from placid, tidal estuaries to turbulent, sea-side cliffs. The reward comes at the end of the trip when your grand entrance past the greasy pole in Gloucester Harbor is followed up with a well-deserved and fresh seafood dinner!

There is more to this circumnavigation than just slugging it out. One must pay close attention to sea conditions throughout the route. Once you exit the Annisquam River and head toward Rockport your bail-out landing options begin to dwindle and you become more committed the further along you go. Beware of fog banks as these move in quickly and of offshore storms as they tend to stir things up along the rocky coastline.

4) Plymouth to Provincetown

The 26 mile open water crossing from Plymouth to Provincetown is a true epic in every sense of the word! To do this the right way, one must launch from Plymouth Harbor (none of this cutting off 6 miles by starting from Manomet crap) and reverse the course that the Pilgrims took in 1620 as they made their way from Race Point in Provincetown. You’ll see a lot of water and maybe a whale or two as you watch the Pilgrim Monument slowly (and I mean slowly) grow on the horizon.  This is definitely one of those trips that will be much more fun in retrospect while boasting your accomplishments over beers a few months later!

The exposure on this trip is intense. There will be times when the nearest land is over 10miles away and there may not be much boat traffic to rely on for help. The P-to-P crossing should be attempted on a cool day with calm seas and a mild SW wind to aid in pushing you across the bay. One would be wise to start the crossing at or slightly before sunrise in order to make sufficient progress before the heat of the day sets in. Also, this is a point-to-point so make sure to have a shuttle set up in Provincetown or contact the Plymouth-Provincetown Ferry to see if they can help get you back in the afternoon.

5) Nantucket Crossing

This is the granddaddy of them all and, to be honest, I’m not even sure how I’d go about making the crossing over to Nantucket. I’ve talked with a few people who launched from Chatham on the Cape and paddled south along the Monomoy Islands for the 35mile trip to Nantucket Harbor all to arrive just in time for a mad dash to catch the last ferry back to the Cape. I have some issues with this route: 1) 35miles is a loooonnnggg day on the water and 2) the route takes you through the upper reaches of Nantucket Shoals which are notorious for producing very nasty conditions when the seas become perturbed.

I’m more interested in making this at least a two day trip. I’d start by taking advantage of the more favorable currents in MV Sound to cross for a night’s stay in Edgartown or Chappaquiddick on Martha’s Vineyard. The second day I’d launch my assault on Nantucket early in the morning when conditions tend to be light and thus allowing ample time to explore the island upon arrival in Nantucket Town. This plan would offer less exposure, shorter crossings, and the time to enjoy a short stay on both islands without scampering to catch the ferry back.

***Disclaimer: Each of these trips presents challenging and potentially dangerous conditions. They’re not recommended for anyone but the most experienced sea kayakers with training in deep water rescue and navigation. This list is intended only to identify the most challenging of the classic sea kayaking trips in coastal Massachusetts and is not intended to provide precise nautical advise as to how one would safety accomplish them. Also, this is not intended to be a competitive “challenge” in any sense as you can certainly be considered an experienced sea kayaker without ever completing a single trip on this list.

Happy and Safe Paddling!

-Kayak Dave

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