What to do and see in Gloucester, Massachusetts (MA): The Best Things to do Good for Big Groups

July 5, 2021 Trinity Boughner

With its sandy North Shore beaches, rocky outcrops, green parks, hemlock woods and wild estuaries full of shorebirds, it is no wonder that Gloucester has attracted such a rich and diverse artists' community. Fitz Hugh Lane, Winslow Homer and John Sloan are just some of the artists who have taken inspiration from Gloucester's beautiful surrounds. Still boasting dozens of galleries and boutiques, as well as museums, theaters and an artists' colony, the city's art scene clearly continues to thrive.
Restaurants in Gloucester

1. Cape Ann Foodie Tours

Excellent
88%
Good
10%
Satisfactory
1%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 200 reviews

Cape Ann Foodie Tours

there are many ways to experience Cape Ann, however none are as fun or as satisfying as our line of food and cultural tours. Choose from our premiere Taste Gloucester Food tour, Rockport Sights and Sweets, Newburport Food Tour and our new Ales and Tales pub tour.

2. Cape Ann Whale Watch

Excellent
86%
Good
10%
Satisfactory
2%
Poor
1%
Terrible
1%
Overall Ratings

5.0 based on 2,726 reviews

Cape Ann Whale Watch

Cape Ann Whale Watch in Gloucester, Massachusetts provides guaranteed whale sightings for every whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of Gloucester deemed one of the "Top 5 Whale Watching Destinations in the World" by the World Wildlife Fund due to the wide variety of whale species whom migrate to the coast of Gloucester, Massachusetts every year to feed on the abundant natural resources. We provide the best whale watching in New England as it's an awe-inspiring experience which every human being should have the opportunity to appreciate. We make it a very special event. For over 35 years, Cape Ann Whale Watch has been dazzling whale watching enthusiasts with sightseeing tours aboard the largest, fastest and most elegant whale watching vessel in Massachusetts, north of Boston, Massachusetts aptly named "The Hurricane II" due to its immense size and speed as it descends upon its destination. Cape Ann Whale Watch's patrons have the opportunity to spend a lot more time with the whales than with other whale watching companies in Gloucester MA since "The Hurricane II" gets to the whales' feeding grounds with much more expediency as well as traveling home faster, therefore more time is actually spent observing whales including but not limited to Humpback Whales, Minke Whales, Northern Right Whales, Pilot Whales, Northern Right Whales, Sperm Whales, Sei Whales, Blue Whales (The Largest Whales in the Seven Seas yet seldom seen around Gloucester MA), Fin Whales, Atlantic White Sided Dolphins, Harbor Porpoises and whole host of other fascinating marine creatures as we deliver the best whale watching excursion in Massachusetts. "The Hurricane II" boasts 115 ft length with over 400 ft of whale watching room from the railings of the upper and lower observation decks for optimum whale watching conditions. There is a heated, furnished indoor cabin with a full service galley serving hot meals, snacks and cold beverages as well as a fully stocked bar with local brews, popular beer, wine and mixed drinks. Cape Ann Whale Watch is truly the finest whale watching tour in the Boston MA area offering the highest level of quality, comfort and service at the cheapest, most affordable price suitable for any family entertainment budget whether on vacation or a day trip. We offer AAA discounts on the adult tickets. We also offer reduced rates for seniors, children and military families. We go where the whales go. Our vessels communicate with each other as to the location of whales so we will go anywhere to see them on the North Shore or South Shore of Massachusetts including off the coast of Boston, Massachusetts: Salem MA, Newburyport, Cape Cod, Hampton NH, Rowley, Rockport MA, Danvers, Peabody, Swampscott, Revere, Winthrop or wherever else the whales may roam.

3. 7 Seas Whale Watch

Excellent
93%
Good
5%
Satisfactory
1%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 2,968 reviews

7 Seas Whale Watch

Trip Advisor's #1 of 26 Tours in Gloucester, 7 Seas Whale Watch has had the privilege of introducing thousands of passengers to the many species of whales and marine wildlife that inhabit the waters from Cape Ann and out to the Stellwagen Bank Marine Sanctuary. Our trips run from mid-April to mid-October and are designed to educate, inspire and provide a deeper understanding and appreciation of our fragile marine environment. We are a family business – Three generations of career captains have worked from this very dock for more than 7 decades. We have a love and respect for the marine environment and a passion for providing the best possible customer experience for you and your family. We look forward to seeing you on the water.

4. Schooner Thomas E. Lannon

Excellent
90%
Good
7%
Satisfactory
2%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 334 reviews

Schooner Thomas E. Lannon

Picture yourself relaxing on the deck of this beautiful 65- foot schooner as she sails out of Gloucester harbor on a light southwesterly breeze. Join us for a two-hour sail and get a taste for what it was like to sail on a fishing schooner a hundred years ago. Help the crew raise the sails, or just sit back and take in the sights and sounds of Gloucester's coastline. Some of our weekend public sails feature music. We offer group rates. And we specialize in private charters for weddings, corporate entertainment, teambuilding, birthdays and more. The Lannon is a great place for a party!

5. Gloucester Stage Company

267 E Main St, Gloucester, MA 01930-4141 +1 978-281-4433 [email protected] http://www.gloucesterstage.com
Excellent
70%
Good
22%
Satisfactory
8%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 37 reviews

Gloucester Stage Company

The Gloucester Stage Company's mission is to present the highest quality professional theatrical productions while contributing to the cultural, economic and educational development of Cape Ann. Open seasonally. Please check our website for current season lineup, seasonal box office hours and to buy tickets. Box Office is open Tuesday - Friday 12-6pm. Additional hours May-October are an hour prior to show times.

6. Good Harbor Beach

99 Thatcher Rd, Gloucester, MA 01930 http://gloucester-ma.gov/index.aspx?nid=299
Excellent
72%
Good
22%
Satisfactory
4%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 693 reviews

Good Harbor Beach

This picturesque curved white-sandy beach with a lazy rolling surf is a favorite among Gloucester residents and visitors.

Reviewed By 81vadimr

Good Harbor beach is one of the best beaches of North Shore in Massachusetts. Deepest and cleanest send. A little island near by with easy access in low tide, just be careful of poison ivy. Parking lot is not very big and filled very quickly in the hot Summer days. Be there before 9am to guarantee the spot. Enjoy it

7. Fishermen's Memorial Monument

Stacy Boulevard, Gloucester, MA +1 978-283-1601 http://www.nps.gov/nr/travel/maritime/glo.htm
Excellent
71%
Good
25%
Satisfactory
4%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 820 reviews

Fishermen's Memorial Monument

Reviewed By stephenfM8666BK - Salem, United States

This memorial has been in its current location for decades, and is dedicated to the fishermen who never came home. Every year, several Gloucester fisher(wo)men are lost at sea. This monument is a testimony to the hard and very dangerous work these men and women do. It has sweeping views of the ocean, and just a few hundred yards awalys a monument to the families who lost a loved one at sea.

8. Capt Bill & Sons Whale Watch

Excellent
76%
Good
15%
Satisfactory
5%
Poor
1%
Terrible
3%
Overall Ratings

4.5 based on 221 reviews

Capt Bill & Sons Whale Watch

Capt. Bill & Sons Whale Watch is a small, family-owned and operated, whale watch company out of Gloucester MA. We take pride in giving the best whale watch tours North of Boston. Join us at Capt. Bills for a 4 hour whale watch trip you will never forget! Each trip is fully narrated by a marine biologist from the Blue Ocean Society, who will teach you all you need to know about these majestic marine mammals and other sea life. Sightings Guaranteed!

9. Stage Fort Park and Beach

Hough Street, Gloucester, MA 01833 +1 978-281-8865 http://gloucester-ma.gov/index.aspx?nid=450
Excellent
63%
Good
29%
Satisfactory
7%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 245 reviews

Stage Fort Park and Beach

This small park overlooking Gloucester harbor marks the spot where the area was first settled in the early 1600s.

Reviewed By Louetta - Georgetown, United States

Stage Fort is really nice. It is right on the ocean and there is a large grassy area, a couple of small beaches, places to cook out, a big snack bar and a long concourse along the beach that you can even walk into town (about a mile). Nice views, right on the ocean. People come in groups and stay for the day. Great for families, you can cook, kids can play on the grass or in the water. There is also a ball field over near the road. I tend to spend my time in the area up past the rest rooms up the hill where there is a smallish beach and plenty of areas to lie out on the rocks above the beach or amongst the trees. All sorts of stuff goes on in this relatively secluded area. I enjoy taking my top off and though I wouldn't on crowded weekends girls do but you might be bothered or photographed. Best wait for weekdays. Parking is kind of expensive. I've heard 15 and I've heard 20. I bicycle so I don't know. Bring your fluids and food if you want. They have full dinners at the snack bar, clams and stuff but a quart of clams is well over $10 plus fries and drinks. It's a stiff walk but there is a well kept concrete walkway all along the edge of the water over the bridge (which opens for boats) and up into town. They have very nice sit down restaurants but you're talking about a mile and a half.

10. Harbor Tours

Excellent
78%
Good
11%
Satisfactory
5%
Poor
2%
Terrible
4%
Overall Ratings

4.5 based on 110 reviews

Harbor Tours

Come aboard and enjoy a fascinating tour of Cape Ann's scenic coastline. Our "Lighthouse Cruise" features up-close views of the six lighthouses on the Island; Or tour America's Oldest Seaport and see a "lobstering" demonstration on our "Harbor Tour". Also, the Gloucester Harbor Water Shuttle and Tour. Hop-on/hop-off. Ticket valid all day. Try our catamaran for a delightful ride around the inner harbor. Our vessels are available for private charters. Discover Gloucester, let us take you there!

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