More Fun Gloucester Destinations You Can Safely Visit

September 02, 2020 / Art and Music, Food and Drink, Good to Know, History/Maritime, Outdoor Adventures, Things to Do & See

The month of September is stunningly beautiful here in Gloucester on Cape Ann. Remember, summer isn’t officially over until September 22. Whether you are a new visitor or know our charming historic seaport inside and out, make some plans to visit us. Wear your mask, keep your 6-ft distance, and come play (by the rules) with us.

Get your FREE Discover Gloucester Guide

As you begin planning your day-trip or getaway to our charming coastal community, order the new Official Discover Gloucester Visitor Guide. In addition to the guide, you will receive access to our website full of Gloucester excursion ideas that include sailing, dining, shopping, whale watching, deep-sea fishing, parks, trails and hikes.
While travel this year will look somewhat different, with a little planning ahead you can be sure to have a memorable and magical visit to Gloucester. To receive a copy and to view the online guide click HERE!
Gataway Mavens Malerie Yolen-Cohen, Discover GloucesterVisitors Welcoming Center at Stage Fort Park

Pick up Discover Gloucester guides, maps, brochures and get some local knowledge from its team of passionate volunteers. Open Thursday – Monday 9:00 am – 3:00 pm. Call for more information 978-281-8865 daily until 6:00 pm. Restrooms open daily 9:00 am – 5:00 pm. Other restrooms at Cape Ann Brewing Co. and The Gloucester House.


Catch a Whale Watch in Gloucester, Cape Ann!

Gloucester Whale Watch companies are now hosting trips. Both 7 Seas Whale Watch7 Seas Whale Watch and Cape Ann Whale Watch have taken the proper precautions to ensure your safety as you embark on a fun-filled tour. Give them a call and make your reservation today!
Schooner Thomas E. Lannon
How about a sail aboard the Lannon? Sit back and relax as you head out through Gloucester’s working harbor and along her rocky coastline. See lighthouses, castles, scenic beaches, and magnificent waterfront homes. Breathe the clean salt air and feel the wind as it fills the schooner’s sails. Sailing through October.
Charter a private sail with Schooner Ardelle Schooner Ardelle
$400 for 2 hours for up to 8 people! And longer options too. Safe, private, affordable, cabin-fever buster. 25% goes to support Maritime Gloucester. Have fun, be active, support local, and do good too. Learn more at
Cruise around Gloucester Harbor with Beauport Cruiselines!

Every Thursday and Saturday – join Beauport Cruiselines for sunset dinner cruises sailing around Gloucester Harbor. Enjoy a classic NewEngland Lobster Bake Dinner, cocktail service and music in the background while taking in the ocean breeze and sweeping views of beautiful Cape Ann. Spend an unforgettable summer night on the water with Beauport Cruiselines. $74 adults/ $45 children under 12. Parties of up to six guests. Top deck seating weather permitting. Click HERE to book!

Yankee Fleet Fishing Adventures
Adventures at Yankee Fleet fishing excursions travel to the areas known as Stellwagen Bank and Jeffrey’s Ledge. With 60 years experience finding the best fishing spots, you are assured to have the best opportunity to catch fish and have fun doing it. Choose from one of their standard trips below or contact them to learn more about private charters.  Yankee Fleet is running trips every day. Full-Day trips 7:00 am – 5:00 pm, $110/person; Marathons on Thursday’s 5:00 am-5:00pm, $130/person; 2 half-day trips daily 8:00 am – 12:30 pm and 1:30 pm – 6:00 pm, $50/person. There is limited capacity on all trips to allow for social distancing. Learn more at
Learn to Surf on Cape Ann
If you’ve always wanted to take a surfing lesson, then look no further than Cape Ann. Surfari teach surf lessons at Good Harbor Beach in Gloucester. Their experienced First Aid (Red Cross) and CPR/AED (American Heart Association) certified instructors offer 60-minute lessons designed to get you out on the water and riding waves in no time! The Surfari experience focuses on all aspects of surfing and ocean awareness and is designed to teach the novice or build on the skills of the more seasoned surfer. Not only will you gain confidence in surfing but also learn about ocean safety and etiquette. Join Christian and crew for an hourly lesson and let them share their love and knowledge of surfing with you. Please contact Surfari by phone at 978-283-SURF or email them to schedule a lesson. For wetsuit sizing,  please have the heights and weights of participants so we can provide the proper fit. Surfing lessons are offered year round. However, with cold New England water and air temps, the end of May through October are your best bets! Call to reserve your surf lesson today!

Harbor Tours Gloucester MA

Explore Gloucester’s Harbor and Coastline on a Harbor Tour
Enjoy a beautiful day out on the water with friends and family! Cape Ann Harbor Tours offers Daily Lighthouse Trips, Harbor Tours/ Lobstering Demonstrations, and Water Shuttle Hourly Trips. It’s such an enjoyable experience to see all that Gloucester Harbor and the Annisquam River have to offer. You’ll be glad you took the ride! Purchase tickets by calling 978-283-1979 or order online
Charlie’s Charters & Sightseeing Tours
Come on an exciting fishing adventure with Captain Scott! Go aboard their  25 foot,  200hp Pro-line vessel. Charlie’s Charters offers a variety of tour options: Private Charters, Sightseeing, Lighthouse Tours, Photo Charters, Seal and Bird Watching, Ash Scattering, Private Scenic, Sunset, Harbor, and River Trips. Photography and Artist charters are available. Free Parking and Free Fish Cleaning and Bagging. Trips depart 7 days a week, 6:00 am and noon from May through October. They prefer to leave at 6:00 am for prime time fishing. Bring your cooler with beverages and light snacks, camera, sunscreen, sunglasses, soft sole shoes and a hat. Cost: $80 per hour with a 2-hour minimum. Reservations: Call 978-281-8992 for a customized trip or email Captain Scott at
Cruise down the Essex River with Essex River Cruises & ChartersEssex River Cruises & Charters
Trip Advisor recently awarded Essex River Cruises & Charters with a 2020 Travelers’ Choice award. Every year, Trip Advisor combs through reviews and ratings from travelers everywhere, and uses that information to award the very best. Essex River Cruises & Charters is in the top 10% of attractions worldwide!  Learn more at Essex River Cruises & Charters.


Beauport, the Sleeper McCann House Guided Tours
Exterior View of Beauport Sleeper McCann

Beauport is opens for guided tours. The tour has been altered to maximize social distancing, and each tour is limited to four guests. Please read the “Know Before You Go” section on the museum’s website at for more information on safety requirements. Advance tickets are required, and admission is free for Historic New England members. Buy tickets HERE.

Beauport, the Sleeper-McCann House, a National Historic Landmark, was the summer home of one of America’s first professional interior designers, Henry Davis Sleeper. Perched on a rock ledge overlooking Gloucester Harbor, Beauport was Sleeper’s retreat, backdrop for entertaining, and professional showcase, and an inspiration to all who visited.
Ravenswood Park Nature

Ravenswood Park offers 600 acres for solitude and quiet contemplation, a testament to its founder’s conservationist philosophy. Nineteenth-century businessman and philanthropist Samuel Sawyer purchased woodlots, old pastures, and swamp near his home on Freshwater Cove, and upon his death left the more than 26 parcels to be turned into a park named Ravenswood, Ravenswood Park is a nature reserve in the western section of Gloucester, Massachusetts owned and managed by the Trustees of Reservations, which acquired the property in 1993. It can be accessed from Western Avenue, the road to Manchester through the Magnolia area. Learn more at

Hammond Castle Museum – Advance Purchase, Timed ticketsHammond Castle, Gloucester MA Photo by CoasttoCoastWithKids
Hammond Castle Museum is open all weekend including Labor Day! Guided tours will continue through the end of October and run on the half hour from 9:30 am to 3:00 pm daily. Thursday evening Candlelight Tours and Spiritualism Tours have been extended through the end of September! Candlelight Tours are at 6:00 pm, 7:00 pm and 8:00 pm. Spiritualism Tours are at 9:00 pm. Advance ticket reservations are required and may be made at . Check the Museum’s website for information about their upcoming Halloween program including The Horror of Abbadia Mare, an adaptation of five H.P. Lovecraft stories! Hammond Castle
Outdoor Yoga Classes with Treetop Yoga
While Treetop Yoga remains a virtual studio with an updated summer schedule, we have added outdoor yoga classes 5 days per week. Participants are required to sign up on our schedule in advance since spaces are limited due to social distancing. All you need is a yoga mat or beach towel and a bottle of water. An all-level class and everyBODY welcome.


The Tastes of Gloucester with Cape Ann Foodie Tours
From delicious local chowder, bacon-wrapped scallops, beer tastings, authentic Italian cannoli, to a sandwich that Gloucester natives have been enjoying for decades. This tour will expose you to local treats you’d be hard-pressed to discover on your own. Along the way, our dynamic tour guides will provide the backdrop to this 400-year-old city with great stories and interesting facts about the oldest working seaport in America. There will be no room for lunch after this tour as they make sure you leave “full” of knowledge! Learn more or sign up at

Great Shops and Restaurants

Savor the flavors at Savour Wine & Cheese  &Private Virtual Kiosk Tasting!
Savour Wine & Cheese
Savour is reserving private tastings now through September 5 (noon to 5:00pm) every half-hour, with 20-minutes devoted to tasting up to 20 bottles from their digital kiosk and the option to acquire choice wines.

Savour continues its popular Curbside Pickup program(subject to change as in-store shopping is temporarily suspended) for a safer shopping experience with its customers accessing everything. Browse their collection of 100+ wines from their popular $14.99 bins, expressing the desired qualities of complexity, gaining length, balance, and finish. Visit Savour’s website for complete ordering details at

Happy Valley Now Open
Located in the quaint coastal city on Cape Ann, Happy Valley’s Gloucester medical and recreational dispensary will be your gateway to enjoying the beauty and history of northeast Essex County like never before. Whether you’re a local or just passing through, a recreational user or a medical marijuana patient, they will have whatever you’ll be looking for, for whatever experience you want to have. Our high-quality products are locally-grown in Gloucester. Learn more at
Ryan & Wood Distillery Hand Sanitizers
Ryan & Wood Distillery is offering their hand sanitizer in a larger (gallon) container. It is being sold at $28/gallon/wholesale. With this pricing, the focus is on helping local restaurants, hospitality, innkeepers and other venues as we continue through this challenging time on Cape Ann. The Liter bottles are also available and may be purchased at Wholesale pricing by the case (12 Bottles)
Stop by for curbside pick up or call ahead for larger orders at 978 281.2282.
Castle Manor Inn Gloucester MA
Grand Summer Porch at The Castle Manor Inn

Dinner: Every Wednesday through Saturday 4:30 – 8:00 pm – Saturday Full Breakfast on the Back Porch 8-11am Sunday Full Breakfast on the Back Porch  9-12Noon PLEASE CALL FOR RESERVATIONS (978) 515-7386.

Woodman’s of Essex
Woodman's of Essex
Fried clams and fresh New England lobsters, steamed clams, shrimp and scallops, creamy clam chowder or a good old-fashioned helping of steamed clams! For over 100 years, Woodman’s of Essex has been offering gluten-free menus with traditional New England lobsters and other seafood, including our famous gluten-free fried clams, to locals and visitors alike. Whether you’re from Boston or Gloucester, Paris or Tokyo, we take pride in serving you the best seafood and #1 best-tasting gluten-free fried clams in America. Learn more or order at
Welcome to Cape Ann Made and Beyond!
A new virtual website that connects artists and makers from New England to interested buyers. Shows have been cancelled so they are now online. It showcases fine art and craft such as painters, printmakers, ceramists, glass artists, jewelers, fibers artists, woodworkers, sculptors and more. Click or search an artist- visit their website and shop from home. Thank you for visiting and supporting the art community. Contact with questions.
Photo by Isaac J. Aiello