Things to Do in Gloucester, MA: Top Sights and Original 3, 5 & 7-Day Itineraries
Gloucester, on Cape Ann north of Boston, is America's oldest seaport, famous for its fishing heritage, The Perfect Storm and some of New England's best whale watching. Beautiful beaches like Good Harbor, the Rocky Neck art colony, Hammond Castle and nearby Rockport make it a perfect coastal getaway.
This guide covers the best things to do in Gloucester, MA, with itineraries for 3, 5 and 7 days, ideas for weekends, couples and families, local food, where to stay and how to get around.
Top things to see in Gloucester, MA
Gloucester Fisherman's Memorial
Man at the Wheel statue.
Whale watching
Stellwagen Bank.
Good Harbor Beach
Sandy beach.
Rocky Neck
Art colony.
Hammond Castle
Medieval-style castle.
Cape Ann Museum
Art and history.
Rockport
Motif No. 1 and Bearskin Neck.
Wingaersheek Beach
Family beach.
Gloucester, MA in 3 days: an original itinerary
1Day 1 · Harbor and history
Start at the Fisherman's Memorial, the 'Man at the Wheel' statue honoring thousands of fishermen lost at sea, then walk the harbor and visit the Cape Ann Museum with paintings by Fitz Henry Lane. Lunch with fried clams. In the afternoon, explore the Rocky Neck art colony and its galleries.
2Day 2 · Whale watching
Take a morning whale watch to Stellwagen Bank, where humpback, minke and fin whales feed from spring to fall. Lunch on the waterfront. In the afternoon, swim or stroll at Good Harbor Beach and walk out to Salt Island at low tide.
3Day 3 · Rockport
Drive to Rockport to see Motif No. 1, the red fishing shack often called the most painted building in America, and browse Bearskin Neck's shops. Lunch with lobster roll. Visit Halibut Point State Park's granite quarry and ocean views.
Gloucester, MA in 5 days
Follow the 3-day plan above, then add these two days:
4Day 4 · Hammond Castle and beaches
Tour Hammond Castle, the eccentric home of inventor John Hays Hammond Jr., then relax at Wingaersheek Beach with its calm water and rocks. Lunch in Annisquam. Sunset at Eastern Point Lighthouse and Dog Bar Breakwater.
5Day 5 · Essex
Visit Essex, birthplace of the fried clam, for antiques and a boat tour of the Essex River marshes. Lunch at Woodman's. Return via Crane Beach in Ipswich. Crane Beach is one of the most beautiful beaches in New England, with dunes and the Castle Hill estate above it.
Gloucester, MA in 7 days
With a full week, keep days 1 to 5 and finish with:
6Day 6 · Boston or Salem
Day trip by train to Salem for witch history or to Boston. Lunch in the city. Return in the evening. The MBTA Rockport Line runs from Gloucester to Boston's North Station in about an hour, with a stop in Salem.
7Day 7 · Farewell
Morning coffee by the harbor, last gallery visit and a farewell lobster dinner overlooking the fishing fleet. Before leaving, pick up smoked fish or local chowder base from a waterfront market as a souvenir of Cape Ann.
What to do in Gloucester, MA on a weekend
Things to do in Gloucester on a weekend? Saturday: harbor, museum and Rocky Neck. Sunday: whale watching and Good Harbor Beach.
St. Peter's Fiesta in late June.
What to do in Gloucester, MA in the evening
In the evening, sunset at Eastern Point.
Seafood shacks.
Gloucester, MA for couples
For couples, whale watching, Rockport and sunset at the lighthouse.
Gloucester, MA with kids
With kids, beaches, whale watching and Hammond Castle.
What to eat in Gloucester, MA
Fried clams
Essex invention.
Lobster roll
New England.
Clam chowder
Classic.
Haddock
Local fish.
Oysters
Fresh.
Where to stay in Gloucester, MA: best areas
Downtown
Harbor.
Rockport
Charming.
Eastern Point
Quiet.
Annisquam
Village.
What to do in Gloucester, MA when it rains
Things to do in Gloucester when it rains? Cape Ann Museum, Hammond Castle and galleries.
How much does a trip to Gloucester, MA cost?
Expect $200–350 per night in summer.
Practical tips for Gloucester, MA
Best time to visit
June–September.
Getting around
Car or commuter rail from Boston.
Our practical tips
- Book whale watches.
- Beach parking fills early.
- Low tide for Salt Island.
- Train from Boston.
- Try fried clams.
- St. Peter's Fiesta.
Mistakes to avoid
- Summer weekend traffic.
- Getting stranded on Salt Island.
- Expecting warm water.
- Off-season closures.
Frequently asked questions
What are the best things to do in Gloucester, MA?
Whale watching, beaches and Rocky Neck.
Best beach?
Good Harbor.
How far from Boston?
About an hour.
Best time?
Summer.