BEACHES

WHALE WATCHING & CHARTER FISHING

KAYAKING & WATER SPORTS

FESTIVALS & EVENTS

PARKS & PLAYGROUNDS

BIRD WATCHING

LIGHTHOUSES

MAN AT THE WHEEL STATUE

TOURS & CRUISE SHIPS

VISITING SAILORS GUIDE

TOURS & CRUISE SHIPS

Cruiseport Gloucester is the spot for cruise ships into Gloucester.  At present, cruise ships do not begin or end their journey in Gloucester.  However, a number of cruise lines make Gloucester a port of call.  If you enjoy cruising, contact your favorite cruise line to see if Gloucester is included in any of the cruises they have to offer.  If not, suggest they make it part of a trip in the future!

Touring by Sea


Cape Ann Harbor Tours  Harbor Loop - (978) 283-1979

Cape Ann Marina's Annisquam River Cruise  75 Essex Avenue - (978) 283-2116

Charlie's Charters - Rose's Wharf, 415 Main St. - (978) 281-8992

Defiance Sail Charters  Beacon Marine,  211 East Main Street - (978) 948-5434

Discovery Adventures Sea Kayaking - (978) 283-3320 / (978) 866-KAYAKER

Schooner Thomas E. Lannon  Rogers Street/Seven Seas Wharf - (978) 281-6634

Seven Seas Harbor Cruises  Rogers Street/Seven Seas Wharf - (978) 283-1776



Narrated Tours

Coastal Visits - Bus tours of the Cape Ann Area - (978) 768-7199

Cape Pond Ice Guided Tours of Historic Ice House  104 Commercial St. - (978) 283-0180

Ryan and Wood Distillery Tour  Blackburn Industrial Park - (978) 281-2282

Tour by Land

Rocky Neck Art Trail - Walk in the footsteps of artists such as Winslow Homer, Fitz Henry Lane and Edward Hopper on this self-guided walking tour through America's Oldest Working Art Colony.

Touring by Bike

Gloucester is so scenic that many visitors enjoy the view by bike. Some of these roadways are very busy so always take care in riding as these are not dedicated bike paths.

Local train service on Saturday and Sunday out of Boston is offering a special car for bikes and bike riders.  Please check on the Transportation page for details.


To East Gloucester, Dogbar Breakwater and Eastern Point Light:

Approximate mileage 11.5 round trip.

Begin at Stage Fort Park Visitor Welcoming Center, R at bottom of hill. Ride along boulevard, follow curve in road past service station L onto Rogers St. At traffic lights, R on East Main St. Possible stops: North Shore Art Assn., & Rocky Neck Art Colony. Enter Eastern Point between stone pillars. Turn R at fork, Beauport Museum on R. Continue to end of road to Lighthouse.

Lock bike if you go out on breakwater. Returning, follow one-way signs. At exit from Eastern Point, go R. (Farrington Ave.) to end; L on Atlantic Rd. to junction of Rte 127A. (Good Harbor Beach is over crest on right). L on 127A (Bass Ave.) to return to starting point.


To Magnolia:

Approximate mileage 7.5 round trip.

Begin at Stage Fort Park Visitor Welcoming Center, L at bottom of hill (near Cupboard). Go L about 1 mi. to Hesperus Ave. Possible stop: Hammond Castle. Continue past museum to Magnolia Sq. (min rotary). Turn L on Magnolia Ave., follow shore, circle back to Magnolia Sq. 

To return to Gloucester, go R on Magnolia Ave. to either Rte 127 (Western Ave.); About 3 miles to starting point.


To Wingaersheek Beach:

Approximate mileage 11.25 round trip.

Begin at Stage Fort Park Visitor Welcoming Center, R at bottom of hill. L at island (Rte. 133). Turn R on Concord St. Continue on Concord at junction with Atlantic St.turn R to Wingaersheek Beach.


(Information taken from Bike Rides in Cape Ann Area by Baness Andrews) 

Touring on Foot - Along the Maritime Trail *


Downtown Loop: Approximate mileage: 1.1 miles. 

Beginning at St. Peter's Park on Rogers St., this walk winds along the waterfront, through the historic downtown district with views of the working waterfront, and past many historic sites and museums.

Stage Fort Park & Stacy Boulevard: Approximate mileage: 1.5 miles round trip.

Begin this walk at the Visitor's Welcoming Center. As you leave the Center turn right (you can take a side jaunt to Ft. Conant and then continue on the water side or return to Center) continue down the hill, turn right at stop sign. Walk along the boulevard past Betty Smith Park and the Fishermen's Wives Memorial Statue, continuing along past the Blynman Canal (draw bridge) and the Fishermen's Memorial Statue also known as the "Man at the Wheel".


Vessels View: Approximate mileage: 2 miles round trip.

This walk encompasses the east part of Main St., an interesting portion of our downtown and working waterfront.

Painter's Path: East Gloucester, approximate mileage: 1.1 miles round trip.

Walk along the path taken by artists who came to Gloucester to paint and write about our rugged coast. Begin the walk at the North Shore Art Association on Pirate's Lane. At the entrance of Pirate's Lane turn right, walk along the water past old seamen's homes, turn right on Rocky Neck, walk to end always bearing right to the Rocky Neck Art Colony.

*This brochure can be obtained at the Visitor Welcoming Center or by calling 1-800-649-6839.

Dogtown Common:

This area was the site of one of Gloucester's earliest settlements. Located off of Cherry Street. There are many trails in this area so make sure you have a map before starting out. Maps can be obtained from the  Visitor Welcoming Center or by calling 1-800-649-6839.

Ravenswood Park

Owned by Trustees of Reservation this is a beautiful wooded park used for walking and cross country skiing as well as biking. It is located on Rte. 127 west of Stage Fort Park.


We strive to have timely and accurate information. If errors are found, we apologize. Please take the time to notify us of any corrections or changes in this listing. Thank you.


Good Harbor Beach at dawn by Joe Ciaramitaro

Harbor Poetry Tour

Explore the beautiful places of Gloucester on this Poetry Tour featuring past and present poets and their words of inspiration.  See Gloucester landmarks and learn our history.

Rocky Neck Art Colony

Gloucester Visitor Welcoming Center at Stage Fort Park
(978) 281-8865 • Email


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Photography on this site courtesy of Jay Albert of Cape Ann Images and Joe Ciaramitaro of Good Morning Gloucester.

Site design courtesy of Valentine Design