Skip to main content
3 min readSpring

Planning the Memorial Day Weekend on Cape Ann

The long weekend is eleven days out. Here is what is open, what is worth booking now, and what the coast actually feels like in late May.

By Dotti Maguire

Drone aerial of Rockport harbor with Bearskin Neck and the breakwater

Memorial Day falls on Monday, May 25 this year. That gives us eleven days. If you are coming for the long weekend, or hosting people who are, this is the week to make the calls that need making. After this, the phones get busier and the good tables fill in.

Here is how we would think about it.

What the weekend actually feels like

Late May on Cape Ann is honest weather. Daytime highs land somewhere between the high 50s and the low 70s depending on the wind. The water is still cold (low 50s), which means morning fog can roll in fast off the harbor and burn off by ten. Bring a fleece for the boat. Bring sunglasses for the afternoon.

The trees are fully leafed out by now. The marsh grass is that almost-neon green it only gets for about three weeks. Lilacs are mostly done; rugosa roses on the dunes are just starting. Hummingbirds are back. Striped bass are in the rivers.

It is not summer yet. The town beaches do not have lifeguards or paid parking enforcement until later. Some seasonal kitchens have soft hours. But the weekend itself, especially Saturday and Sunday, is the first real crowd of the year. Bearskin Neck will be busy. Good Harbor parking will fill by 10am if the forecast holds.

Book these now

A few things tend to sell out for Memorial Day weekend and are worth grabbing this week:

  • A whale watch. Cape Ann Whale Watch and 7 Seas Whale Watch are both running daily now. The naturalists have been seeing humpbacks on Stellwagen for a couple of weeks, including some familiar names. Pick a morning trip if you are fog-averse; afternoons tend to clear.
  • Dinner Saturday night. The harbor-view rooms book first. Tonno, Franklin Cape Ann, 1606 at the Beauport, and Causeway all take reservations and all fill up. If you want to walk in somewhere, aim for Tuesday or a 5pm Saturday seating.
  • A schooner sail. Schooner Ardelle's season is starting up out of Maritime Gloucester. Two-hour sails, weather dependent, and a small boat by design.
  • A fishing charter. Tuna Tail and Coastal Fishing Charters are both taking dates. Striped bass season is on; tuna comes later.

If you are staying with us and want a specific recommendation for your group, email and we will point you. Some of these things are easier to walk into than others.

What is actually open

Hammond Castle has been open since April 28 and is a good rainy-day or jet-lagged-kid play. The grounds alone are worth the walk. Rockport Art Association's spring shows are up. The Shalin Liu has performances most weekends.

The Cape Ann Museum downtown is still closed for renovation and reopens June 30, so save that one for July. The Rockport Farmers Market does not start until June 14.

On the food side: Woodman's in Essex is in full swing. J.T. Farnham's and Essex Seafood are open for clams in the rough. The Lobster Pool up at Folly Cove is doing sunset crowds again, which is the whole reason to go. Roy Moore Lobster Company on Bearskin Neck is the easy lunch.

For breakfast, Sugar Magnolias has settled into the new Main Street location nicely. Brothers' Brew in Rockport handles the coffee-and-donut version of the same idea.

A workable Saturday

If you want a template: coffee somewhere on Main Street in Gloucester by 8. Drive out to Halibut Point in Rockport by 9:30, walk the quarry loop and out to the overlook, which takes about an hour. Lunch on Bearskin Neck or back in Rockport center. Afternoon at Good Harbor or Wingaersheek if the sun is out, or the Hammond Castle grounds if it isn't. Dinner reservation at 7. Drink afterward at the Rhumb Line or somewhere quieter, depending on whether there is music on.

Sunday is for the lower gear: a long breakfast, a walk on the HarborWalk, a bookstore, the drive home through the marsh on 133.

The thing to remember

Memorial Day weekend is the first weekend the Cape feels like its summer self, but the weather still gets a vote. Have one indoor plan in your back pocket. Pack a layer. And book the Saturday dinner this week, not next.

Questions about your specific dates, email us. We answer.

SpringMayGloucesterRockportMemorial Day
Come see it for yourself

Every home is one we'd stay in.

Browse the Homes
Stay nearby

A few of the homes.

Browse all homes