Affiliate disclosure: As an Amazon Associate, we may earn commissions from qualifying Amazon.com purchases

Things To Do In Gloucester Massachusetts: Outdoor Activities, Cultural Attractions, Dining And Shopping, Historical Sites, And Events

Explore Gloucester Massachusetts and enjoy a range of outdoor activities like whale watching and fishing charters, visit cultural attractions such as Gloucester Harborwalk and Cape Ann Museum, indulge in delicious seafood at local restaurants, explore historical sites like Gloucester Fisherman’s Memorial, and immerse yourself in exciting events like St. Peter’s Fiesta and the Rocky Neck Holiday Art & Fine Crafts Festival.

Outdoor Activities in Gloucester Massachusetts

Gloucester, Massachusetts offers a wide range of outdoor activities that will satisfy the adventurer in you. Whether you’re a nature lover or seeking thrilling experiences, this charming coastal city has something for everyone. From whale watching to fishing charters, from relaxing on the beaches to kayaking and paddleboarding, Gloucester is a haven for outdoor enthusiasts.

Whale Watching

One of the most popular outdoor activities in Gloucester is whale watching. Imagine being surrounded by the vast Atlantic Ocean as you witness these magnificent creatures in their natural habitat. Gloucester boasts several reputable whale watching companies that provide unforgettable experiences. Hop on a tour boat and embark on a thrilling adventure as you search for humpback, finback, and minke whales. Marvel at their graceful movements and listen to their awe-inspiring songs. It’s an experience that will leave you in awe of nature’s wonders.

Fishing Charters

For those who love fishing or want to try their hand at it, Gloucester offers excellent fishing charters. Whether you’re an experienced angler or a novice, these charters cater to all skill levels. Join a knowledgeable captain and crew as they guide you to the best fishing spots in the area. With a variety of fish species available, including striped bass, bluefish, and cod, you’re sure to have an exciting and rewarding fishing experience. Don’t forget to bring your camera to capture the moment when you reel in your first catch!

Beaches and Parks

Gloucester is blessed with stunning beaches and parks where you can relax, soak up the sun, and enjoy the refreshing ocean breeze. Good Harbor Beach, known for its soft sand and clear waters, is a favorite among locals and visitors alike. Take a leisurely stroll along the shore, build sandcastles, or simply bask in the beauty of the surroundings. Wingaersheek Beach is another picturesque spot with its calm waters and scenic views. Pack a picnic and spend a day enjoying the beachside serenity.

If you prefer exploring nature’s wonders, Gloucester has several parks to satisfy your cravings. Stage Fort Park is a historic gem that offers breathtaking views of Gloucester Harbor. Take a walk along the harborwalk trail and marvel at the beauty of the coastline. Ravenswood Park is a nature lover’s paradise, with its tranquil forests, serene ponds, and well-maintained trails. Immerse yourself in the serene atmosphere and let the sights and sounds of nature rejuvenate your soul.

Kayaking and Paddleboarding

For those seeking an active adventure on the water, Gloucester provides opportunities for kayaking and paddleboarding. Explore the picturesque coastline, paddle through tranquil coves, and discover hidden beaches. Rent a kayak or paddleboard from one of the local outfitters and set off on your own expedition. Glide along the water, feeling the rhythm of the waves beneath you and immersing yourself in the serenity of the surroundings. Whether you’re a beginner or an experienced paddler, Gloucester’s calm waters and stunning scenery make it the perfect destination for these water activities.


Cultural Attractions in Gloucester Massachusetts

Gloucester, Massachusetts is not only known for its stunning natural beauty and outdoor activities but also for its vibrant cultural attractions. From scenic harbor walks to renowned museums and art colonies, there is something for everyone to explore and enjoy in this charming coastal town.

Gloucester Harborwalk

One of the must-visit cultural attractions in Gloucester is the Gloucester Harborwalk. This picturesque pathway meanders along the waterfront, offering breathtaking views of the harbor, fishing boats, and the city skyline. As you stroll along the Harborwalk, you’ll come across various historical markers and plaques that provide fascinating insights into Gloucester’s maritime heritage.

  • Take a leisurely walk along the Harborwalk and immerse yourself in the rich history of Gloucester.
  • Admire the traditional fishing boats and observe the bustling activity of the harbor.
  • Stop by the Fishermen’s Wives Memorial, a poignant tribute to the brave women who supported the local fishing industry.

Cape Ann Museum

For art enthusiasts and history buffs, the Cape Ann Museum is an absolute gem. This museum showcases the region’s rich artistic and cultural heritage, with a particular focus on the artists who have been inspired by Gloucester’s breathtaking landscapes.

  • Explore the museum’s extensive collection of paintings, sculptures, and photographs that depict Gloucester’s coastal beauty.
  • Learn about the artistic movements and influential artists who have shaped Cape Ann’s creative scene.
  • Don’t miss the fascinating exhibits that delve into Gloucester’s maritime history, showcasing the town’s deep connection to the sea.

Rocky Neck Art Colony

Nested within a charming neighborhood, the Rocky Neck Art Colony is a vibrant hub for artists and art enthusiasts alike. This historic art colony has been attracting creative minds since the early 19th century, and it continues to thrive as a haven for painters, sculptors, and craftsmen.

  • Take a stroll through the quaint streets of Rocky Neck and discover the numerous galleries and studios showcasing a wide range of artistic creations.
  • Engage with local artists and gain insight into their creative processes during open studio events.
  • Immerse yourself in the lively atmosphere of Rocky Neck, especially during the annual Rocky Neck Art Colony’s Summer and Winter Art Festivals.

Hammond Castle Museum

Perched atop Gloucester’s scenic shoreline, the Hammond Castle Museum is a truly unique cultural attraction. Built in the style of a medieval castle, this architectural marvel houses an impressive collection of medieval artifacts, Renaissance artwork, and even a medieval-style chapel.

  • Step back in time as you explore the castle’s grand halls, secret passageways, and lush gardens.
  • Marvel at the intricate craftsmanship of medieval armor, weaponry, and antique furniture.
  • Attend one of the castle’s special events, such as medieval-themed dinners or live performances, which bring the rich history of the castle to life.

Gloucester, Massachusetts is a treasure trove of cultural attractions that seamlessly blend history, art, and natural beauty. Whether you’re strolling along the Gloucester Harborwalk, immersing yourself in the artistic ambiance of the Cape Ann Museum, exploring the vibrant Rocky Neck Art Colony, or stepping into the medieval world of the Hammond Castle Museum, you’re sure to be captivated by the unique experiences that await you in this coastal town.


Dining and Shopping in Gloucester Massachusetts

When you visit Gloucester, Massachusetts, you’ll find a variety of dining and shopping options that cater to all tastes and preferences. Whether you’re a seafood lover, a fan of local boutiques, or enjoy browsing through farmers markets, Gloucester has something for everyone. Let’s explore the diverse culinary and retail scene in this charming coastal town.

Seafood Restaurants

Gloucester is renowned for its fresh seafood, and you’ll find a plethora of restaurants that specialize in serving delectable ocean delicacies. From casual dining spots to upscale eateries, there’s a seafood restaurant to suit every occasion and budget.

  • Captain Carlo’s: Located right on the waterfront, Captain Carlo’s offers a picturesque dining experience with panoramic views of Gloucester Harbor. Indulge in their famous lobster rolls, clam chowder, or try their catch of the day for a truly authentic taste of the sea.
  • The Gloucester House: Situated in the heart of downtown Gloucester, The Gloucester House has been a local favorite for over 50 years. Enjoy their extensive menu featuring classics like baked haddock, fish and chips, and their signature seafood casserole.
  • The Lobster Pool: For a more laid-back atmosphere, head to The Lobster Pool, nestled along the rocky coastline. Feast on their mouthwatering lobster dishes while enjoying the breathtaking views of Ipswich Bay. Don’t forget to try their famous lobster roll!

Local Boutiques and Shops

Gloucester boasts a vibrant shopping scene with an array of local boutiques and shops that offer unique and one-of-a-kind treasures. Whether you’re looking for clothing, home décor, or handmade crafts, you’ll find it all in Gloucester.

  • Main Street: Take a stroll down Main Street, where you’ll discover a charming collection of boutiques and specialty stores. From fashion boutiques offering the latest trends to quaint shops selling handmade jewelry and accessories, Main Street has something for every fashion-savvy shopper.
  • Cape Ann Olive Oil Company: This delightful shop on Rogers Street is a haven for food enthusiasts. Step inside and explore their wide selection of gourmet olive oils, balsamic vinegars, and specialty food products. The friendly staff is always ready to provide recommendations and let you sample their delicious offerings.
  • The Bookstore of Gloucester: Bookworms will feel right at home in this cozy independent bookstore located on Main Street. Browse through their extensive collection of books, from bestsellers to local literature, and indulge in a quiet afternoon of literary exploration.

Farmers Markets

For those who appreciate fresh, locally sourced produce, Gloucester’s farmers markets are a must-visit. These vibrant marketplaces are not only a great way to support local farmers but also an opportunity to immerse yourself in the community’s vibrant atmosphere.

  • Gloucester Farmers Market: Held every Thursday at Stage Fort Park, the Gloucester Farmers Market offers a wide variety of fresh fruits, vegetables, baked goods, and artisanal products. Engage with the friendly vendors, learn about their farming practices, and savor the flavors of Gloucester in every bite.
  • Rockport Farmers Market: Just a short drive from Gloucester, the Rockport Farmers Market is another excellent option for locally grown produce and homemade goods. With its picturesque location overlooking Rockport Harbor, this market provides a beautiful backdrop for your shopping experience.

Artisanal Crafts and Gifts

If you’re looking for unique souvenirs or special gifts, Gloucester is brimming with shops that showcase the talents of local artisans. From handmade crafts to exquisite artwork, you’ll find plenty of options to bring a piece of Gloucester’s artistic spirit home with you.

  • Rocky Neck Art Colony: Located in East Gloucester, the Rocky Neck Art Colony is a haven for art enthusiasts. Stroll through this vibrant neighborhood and explore the numerous galleries and studios showcasing a wide range of artwork, including paintings, sculptures, and photography.
  • The Cultural Center at Rocky Neck: This community-based arts organization serves as a hub for creativity and cultural events. Visit their gallery and shop, where you can purchase unique artwork and crafts made by local artists. You might even have the opportunity to meet the artists themselves and learn about their creative process.
  • Cape Ann Lighthouse Tours and Gifts: Located at the entrance to Stage Fort Park, this gift shop offers a variety of nautical-themed items and lighthouse-inspired souvenirs. Find the perfect memento to remind you of your time in Gloucester or pick up a thoughtful gift for a loved one.

In Gloucester, Massachusetts, dining and shopping experiences are as diverse as the town itself. Whether you’re indulging in fresh seafood, exploring local boutiques, or immersing yourself in the vibrant arts scene, Gloucester has something to offer every visitor. So, don’t miss the opportunity to savor the flavors, discover unique treasures, and immerse yourself in the rich cultural tapestry of this charming coastal town.


Historical Sites in Gloucester Massachusetts

Gloucester, Massachusetts is steeped in rich history and is home to several fascinating historical sites. From monuments honoring the city’s fishing heritage to well-preserved landmarks, there is much to explore and discover. Let’s delve into some of the historical sites that make Gloucester a captivating destination.

Gloucester Fisherman’s Memorial

One of the most iconic landmarks in Gloucester is the Gloucester Fisherman’s Memorial. This monument stands tall and proud, overlooking the harbor, paying homage to the brave men and women who have lost their lives at sea. It serves as a somber reminder of the dangers faced by Gloucester’s fishermen and their contributions to the city’s maritime legacy.

The Fisherman’s Memorial features a bronze statue of a fisherman, with his eyes fixed on the horizon, standing atop a granite base. Inscribed on the base are the names of those who have lost their lives while fishing. The memorial is a place of reflection and remembrance, inviting visitors to pay their respects and honor the sacrifices made by Gloucester’s fishing community.

Stage Fort Park and Visitor Center

Stage Fort Park is a historical site that offers not only scenic beauty but also a glimpse into Gloucester’s past. This picturesque park sits on a peninsula, providing stunning views of Gloucester Harbor and the Atlantic Ocean. It is a popular spot for picnicking, walking, and enjoying outdoor activities.

Within Stage Fort Park, you’ll find the Visitor Center, where you can learn more about the history of Gloucester. The center showcases exhibits that highlight the city’s early settlers, its maritime heritage, and the role it played in the American Revolution. Visitors can immerse themselves in the stories and artifacts that bring Gloucester’s past to life.

Annisquam Village Church

Nestled in the charming village of Annisquam, the Annisquam Village Church is a historical gem that has stood the test of time. Built in 1830, this beautiful church is a fine example of New England architecture and a testament to the community’s enduring spirit.

The Annisquam Village Church is not only a place of worship but also a cultural hub. It hosts various events throughout the year, including concerts, art exhibitions, and community gatherings. Its stained glass windows, classic white facade, and serene surroundings make it a captivating sight for visitors seeking a glimpse into Gloucester’s architectural and cultural heritage.

Beauport, the Sleeper-McCann House

Beauport, also known as the Sleeper-McCann House, is a historic house museum that offers a unique window into the life and style of a bygone era. Located on Eastern Point, this enchanting mansion was once the summer retreat of Henry Davis Sleeper, a renowned interior decorator.

Step inside Beauport, and you’ll be transported to a world of opulence and creativity. Each room is meticulously designed and adorned with a vast collection of antiques, artwork, and curiosities. From the grandeur of the Great Hall to the whimsical charm of the Octagon Room, every corner tells a story and showcases Sleeper’s exceptional taste.

Beyond its architectural and design marvels, Beauport boasts breathtaking views of the ocean and meticulously manicured gardens. It’s a place where visitors can immerse themselves in history, art, and natural beauty.


Events and Festivals in Gloucester Massachusetts

Gloucester, Massachusetts, is not only known for its breathtaking natural beauty and rich cultural heritage, but it is also home to a vibrant calendar of events and festivals that attract visitors from near and far. Whether you’re a history buff, an art enthusiast, or simply looking for a good time, Gloucester has something for everyone. Let’s take a closer look at some of the most exciting events and festivals that you can experience in this charming coastal city.

St. Peter’s Fiesta

One of the most anticipated events in Gloucester is the annual St. Peter’s Fiesta, a celebration deeply rooted in the city’s Italian-American heritage. Held in late June, this festival pays homage to St. Peter, the patron saint of fishermen and the protector of Gloucester’s seafaring community.

During the festival, the streets of Gloucester come alive with colorful parades, traditional processions, and lively music. Witness the spectacle of the greasy pole competition, where brave participants attempt to traverse a slippery pole to claim the flag at the end. Indulge in delectable Italian cuisine, enjoy live entertainment, and immerse yourself in the vibrant atmosphere that fills the air.

Schooner Festival

For sailing enthusiasts and lovers of maritime history, the Schooner Festival is an event that should not be missed. Every Labor Day weekend, Gloucester hosts this grand gathering of majestic schooners, showcasing the city’s rich seafaring heritage.

Witness the awe-inspiring sight of these magnificent vessels as they gracefully navigate the waters of Gloucester Harbor. Take part in exciting races, watch schooners being beautifully rigged, and even have the opportunity to step aboard some of these historic ships. The Schooner Festival is a true celebration of Gloucester’s maritime legacy that will leave you with a deep appreciation for the art of sailing.

Gloucester Waterfront Festival

If you’re looking for a family-friendly event filled with fun, food, and entertainment, the Gloucester Waterfront Festival is the perfect choice. Held annually in August, this festival transforms the city’s waterfront into a bustling hub of activity.

Explore rows of vendor booths offering a wide array of arts, crafts, and delicious food. From handmade jewelry and pottery to unique clothing and accessories, you’ll find something for every taste and preference. Take a break from shopping and enjoy live music performances, street entertainers, and interactive activities for children. With its lively atmosphere and picturesque setting, the Gloucester Waterfront Festival guarantees a memorable day out for the whole family.

Rocky Neck Holiday Art & Fine Crafts Festival

Embrace the holiday spirit and immerse yourself in the world of art at the Rocky Neck Holiday Art & Fine Crafts Festival. Held annually in December, this festival showcases the talents of local artists and craftsmen, making it the perfect place to find unique gifts for your loved ones.

Stroll through the festively decorated booths and admire a wide range of artwork, including paintings, sculptures, ceramics, and jewelry. Engage in conversations with the artists, gain insight into their creative processes, and even purchase one-of-a-kind pieces directly from the makers themselves. The Rocky Neck Holiday Art & Fine Crafts Festival is a true celebration of Gloucester’s vibrant arts scene and a wonderful way to support local talent.

In conclusion, Gloucester, Massachusetts, is a city that knows how to celebrate. From the lively St. Peter’s Fiesta to the majestic Schooner Festival, the Gloucester Waterfront Festival, and the artistic charm of the Rocky Neck Holiday Art & Fine Crafts Festival, there is an event or festival to suit every taste and interest. So, mark your calendar, pack your bags, and get ready to immerse yourself in the vibrant spirit of Gloucester’s events and festivals. You won’t be disappointed!

Leave a Comment