Past Garden Tours

Generous Gardener’s primary annual fundraiser is our Gloucester Garden Tour.  This event began in 2013 to raise funds for flowers at the Fishermen’s Wives Memorial.  Each year in a different part of Gloucester, generous garden owners open their private spaces to the public for one day to benefit all of the public gardens in Gloucester.  

Past Garden Tours


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Explore gorgeous private gardens along Gloucester’s stunning Back Shore.

Traveling along the Back Shore is to experience the grandeur of the Atlantic Ocean in its full glory. The magnificent vistas include Good Harbor Beach, the twin lighthouses on Thacher Island, and the waves crashing along miles of rocky shore. When French explorer Samuel de Champlain visited the area in 1606 he named it Le Beau Port meaning the beautiful harbor, and on this tour, you will easily understand why.

This year’s Generous Gardeners’ Garden Tour will provide the opportunity to see hidden backyard gardens behind many of the impressive facades on Atlantic Road and neighboring roads.  One iconic property on Sherman Point is 3.5 acres of manicured lawn and gardens that served as a small golf course for the original owner. 

Tickets are $30 each and may be purchased the day of the tour at the Stop & Shop parking lot, 6 Thatcher Road, Gloucester, or in advance below.

This is a self-guided walking tour of 3 miles roundtrip from Stop & Shop.

Photography welcome | No pets | Rain or Shine

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The sixth annual Gloucester Garden Tour was in the intriguing Lanesville neighborhood.  Over 600 visitors explored more than a dozen lovely private gardens, quarries and enjoyed the gorgeous ocean views.  Originally accessible only by stagecoach, Lanesville is the northern-most neighborhood of Gloucester. In the 1800’s Lanesville granite was quarried, cut and shipped from Lanes Cove via “granite sloops” to pave roads in New York, Philadelphia and Boston. Even the stone overpasses of Route 128 were constructed with Lanesville granite in the 1950’s. The granite industry was active in the area for over one hundred years. Scenes from the granite quarrying business and related themes appear in artwork created by artists who discovered the neighborhood. Paul Manship and Walker Hancock both built their studios on abandoned quarries in the 20th century. Virginia Lee Burton established her famous Folly Cove Designers and wrote children’s books still beloved today, including Mike Mulligan and His Steam Shovel. Today, Lanesville continues to inspire artists and authors.


The fifth annual Gloucester Garden Tour was in the historic neighborhood of Magnolia.  Attendees toured 14 impressive gardens, including one designed by the famous Olmsted firm. The village of Magnolia straddles the border of Gloucester and Manchester-By-The-Sea. In its heyday, Magnolia was a fashionable destination for the wealthy to summer. The huge Oceanside Hotel and the smaller Magnolia Manor drew the rich and famous to the village. There were posh stores like Tiffany’s lining Lexington Avenue and mansions along Shore Road.  Today Magnolia is a quiet residential neighborhood but it still retains remnants of grander days. This tour was a  a varied mix of cottage gardens, rose gardens and estate gardens with fabulous ocean views as you strolled along Shore Road. 


Gloucester is a city of neighborhoods and Eastern Point is undeniably the most exclusive of all. Eastern Point has been settled since at least 1728, but it was after 1887 that it became a vacation spot for the wealthy who built magnificent “cottages.” This neighborhood is so exclusive that a State Supreme Court ruling in 1859 actually affirmed the right to bar the public from entering Eastern Point. Fortunately, visitors were allowed to pass through the stone gates and view 11 incredible estate gardens.  In addition, Historic New England opened the gardens of Beauport, the historic home built by Henry Sleeper from 1907 to 1934


in 2015 Generous Gardeners presented a walking tour of 15 gardens in the Annisquam village neighborhood of Gloucester. The village of Annisquam was first settled in 1656. Annisquam is said to be an Indian name, “squam” being the Indian word for harbor, but the early settlers found no evidence of natives. They developed the village for shipbuilding and eventually for trade. Much later it became popular as a summer resort. Many of the houses in the village are historic and the architecture is quintessential New England. Vehicular traffic is very limited by a single entry road into the village. A drawbridge, built in 1847 over Lobster Cove, once served carriages but it was replaced in the late 1980’s by the current pedestrian-only footbridge. The footbridge is a rare example of a wood pile and timber stringer bridge and is listed on the National Register of Historic Places.


 The second Generous Gardeners tour included 12 fabulous gardens located along the Back Shore of Gloucester.  Some of the gardens were expansive, others were intimate, and many had breathtaking ocean views. In addition, one of the gardens featured a unique “man cave” and another garden included a classic car collection. 


Generous Gardeners held the first garden tour in West Gloucester.  Hillary Holdsworth opened her wonderful gardens, and Susan Kelly and other Biskie Head Neighbors were also on this tour.  Generous Gardeners also included the (then) small Stacy Boulevard Gardens.