The Week the Water Warms Enough to Think About Boats
May's first full week is when Cape Ann shifts from looking at the water to getting on it. Here is what is open, what is starting, and what to do in between.
By Dotti Maguire
There is a week in early May when the harbor stops being a postcard and starts being a place where things happen. Masts go up. Mooring lines get checked. The hum of an outboard at 7 a.m. replaces the quiet of April. This is that week.
The water is still cold (mid-fifties, give or take), so nobody is swimming yet. But the working harbor is fully awake, the whale watch boats are running, and a handful of seasonal places have flipped their signs from CLOSED to OPEN. If you are coming up this week, here is what the Cape actually looks like right now.
On the water
Whale watching season is on. Both Cape Ann Whale Watch and 7 Seas are sailing daily out of Gloucester Harbor, and early May is honestly one of the better windows. The humpbacks have been on Stellwagen Bank for a few weeks, the boats are not yet packed with summer crowds, and the light on the water at 4 p.m. in May is something else. Bring a warm layer. It is colder offshore than it is on land, always.
If you want something quieter, Beauport Cruiselines runs harbor tours that stay closer in, and the Schooner Ardelle is sailing out of Maritime Gloucester starting this month. A two-hour sail on the Ardelle in May, with maybe a dozen people on deck instead of forty, is the version of Cape Ann we keep telling friends about.
For the do-it-yourself crowd, North Shore Adventures in Rockport has kayaks and bikes ready to rent. Front Beach in Rockport and the Annisquam are both reasonable put-ins this time of year, though the wind tends to come up in the afternoon. Morning paddles are the move.
What just opened
Little Sister opened for the season on Bearskin Neck back on April 10, and they have settled into Friday-through-Sunday hours, 11 to 7. A burger and a beer on the deck at 4 p.m. on a May Saturday, with the harbor right there, is one of the better small pleasures the Cape offers.
The Lobster Pool in Folly Cove is open. If you have never been: it is BYOB, it sits on the rocks at the north end of the Cape, and the sunset view is the actual reason to go. The food is good. The view is the thing.
Hammond Castle Museum opened for its 2026 season on April 28. Walking the grounds in early May, before the summer crowds, with the ocean a hundred feet below and the gardens just starting to fill in, is a particular kind of Cape Ann afternoon. Give it two hours.
A note for museum people: the Cape Ann Museum's downtown campus is still closed for renovation and reopens June 30. CAM Green reopens July 10. If a museum visit is on your list, the Rockport Art Association is open and has their annual auction coming up on May 2, and Sargent House in Gloucester is doing centennial programming all year.
What is still a few weeks out
We say this every May, but: not everything is open yet, and that is fine. The Rockport Farmers Market starts June 14. Saint Peter's Fiesta is June 24 through 28. The Rockport Chamber Music Festival kicks off June 12 at Shalin Liu. Some of the smaller seasonal shops on Bearskin Neck are still on weekends-only or not yet flipped. If you walk the Neck on a Tuesday this week, expect maybe half the shops to be open. On a Saturday, more.
This is the trade. You get the Cape without the crowds, but you get fewer hours and fewer options. We think it is worth it.
A reasonable Saturday
If you want a template: start with coffee and a donut at Brothers' Brew in Rockport, walk Bearskin Neck before 11 when it is still quiet, drive up to Halibut Point for an hour on the trails (the quarry, the lookout, the granite ledges that drop into the Atlantic), come back down for a late lunch at Roy Moore Lobster Company or a burger at Little Sister, and end the day with a sunset at Folly Cove. If you have energy left, the Rhumb Line in Gloucester usually has something on Saturday nights.
If the weather turns (and it might, this is May on the North Shore), pivot to Tonno or Causeway for an early dinner, or post up at Pleasant Street Tea Co. with a book for an hour and let the rain pass. It usually does.
The actual point
May is not the Cape at full volume. It is the Cape tuning up. The boats are testing engines, the kitchens are training new staff, the gardens are halfway in. If you like watching a place wake up, this is the week to be here.