Top Spots for a Bike Tour Around Gloucester 

May 01, 2023 / Food and Drink, Things to Do & See

Spring is the perfect time to enjoy the many historic landmarks, sandy beaches, and unique dining spots in Gloucester. If you love to explore while on your bike, even better! Gloucester is the perfect spot to spend the day and experience some historic landmarks, scenic vistas, cultural attractions, and (of course) some delicious food. 

Whether you are a novice cycler or one who spends every weekend exploring cities and towns along the shore, Gloucester has a few places that will allow you to enjoy the outdoors on your bike.

If you are seeking a day trip on your bike here is a fun tour from Hammond Castle along Route 127 along the waterfront and out to the Eastern Point Lighthouse viewing area. This bike tour hits several of the major sights Gloucester is known for. 

Walking Map of City of Gloucester, Massachusetts

Hammond Castle Museum

Located at 80 Hesperus Avenue, along the picturesque Atlantic coast of Gloucester sits the unique treasure of Hammond Castle Museum. Before you begin your bike tour along the coast of Gloucester and the working harbor, visitors can take a self-guided tour of the grounds and interior of this European-style castle. While there you will be able to see the 12th & 13th Century Arches, Look Out Point, the Bell Tower, and the iconic Drawbridge. 

While bikes are prohibited from the grounds, you can use this as a starting point from which to begin your bike exploration of Gloucester. 

Ravenswood Park 

Continuing on your bike journey, either with friends, family or as a lone biker, you won’t want to miss Ravenswood Park on your way out of Hesperus Avenue. Take a left on Route 127 and you will quickly find the main entrance of this beautifully preserved park. 

Explore more than 10 miles of crushed stone pathways that pass by woody areas, pastures, and even a view of Gloucester Harbor. 

Revolutionary War Cannon at Stage Fort Park, Gloucester MA

Revolutionary War cannon at Stage Fort Park. Photo Credit: Michelle Williams

Stage Fort Park & Half Moon Beach 

Now that you have enjoyed the architectural splendor and natural woodland surroundings of Gloucester, it’s time to head your bike toward downtown Gloucester. On your way down Western Avenue, you will see Stage Fort Park where you can stop to admire the scenery, have a picnic, or get a quick snack at the Cupboard at Stage Fort Park

While at Stage Fort Park, don’t forget to explore Half Moon Beach where you can dip your toes before continuing on your journey. 

Fisherman’s Memorial and Pavillion Beach 

As you continue on your bike tour following the coastline, you will come to the Pavillion where you can view the iconic Fisherman at the Wheel, the Fishermen Wives Memorial, and WWII Memorial. 

The Fisherman at the Wheel statue stands 8 feet tall and was completed in 1925 in honor of Gloucester’s 300th Anniversary. Now, nearly one hundred years later, the fisherman gazes out over the water, ready for potential danger on the ocean that still impacts the thousands of visitors each year. 

Further down Stacy Boulevard, The Fishermen’s Wives Memorial stands in honor of the patience and fortitude of the wives and children who wait for the safe return of their fishermen. 

Pavilion Beach, on the eastern end of Stacy Boulevard, is yet another stop along your bike journey where you can sit and enjoy the views or break for a quick walk on the sand. During St. Peter’s Fiesta in Gloucester in June, this beach becomes a prime viewing for the Greasy Pole contest. 

Downtown Gloucester bustles with activity in the summer. Photograph by Elise Sinagra

Downtown Gloucester bustles with activity in the summer. Photograph by Elise Sinagra

Downtown Gloucester 

Now that your bike ride has taken you from Hammond Castle Museum to Ravenswood Park, Stage Fort Park, and down Stacy Boulevard, you have probably worked up quite the appetite. Head along the shoreline to Downtown Gloucester where you will find many options from coffee shops and sandwich shops where you can grab a quick bite to restaurants where you can enjoy a more leisurely meal. 

There are so many great eateries to enjoy,  depending on your level of hunger and what you are craving, any of them will make for a perfect stop in the downtown region before you head to your next bike stop. You are sure to love 2 Sister’s Coffee Shop, Jim’s Bagel and Bake Shoppe, Virgilio’s Italian Bakery, and Drift Cafe if you are hankering for a sandwich or cup of joe. Visit for a full list of Gloucester’s delicious restaurants.

Rocky Neck Art Colony and Cultural Center 

Now that you have satisfied your hunger, it’s time to head back out to explore more of Gloucester. Continuing around the harbor you will not only be able to witness the hardworking men and women who haul in catches for the day but you will also come upon the Rocky Neck Art Colony and Cultural Center. Here you can view working galleries and studios and speak with the artists themselves. Wander from gallery to gallery as you explore the many mediums that these talented artists use. You will definitely want to come back after your visit to delve deeper into this cultural community. 

Eastern Point Wildlife Sanctuary 

To round out your bike tour, stop at the Eastern Point Wildlife Sanctuary. Located on Eastern Point Boulevard you can view butterflies and unique seabirds. Don’t forget to bring your camera as you can also view Eastern Point Lighthouse along your journey. 

While this bike tour is just under 7 miles, your day will be filled with the unique wonders of Cape Ann and Gloucester, from a medieval-style castle to historical landmarks and sandy beaches to the art of a working art colony. There is something for everyone along the coast of Gloucester this spring. Looking for more? Find another scenic Cape Ann bike route here.