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Located on the picturesque shores of Cape Cod Bay, Plymouth, Massachusetts, is renowned as the site of the Pilgrims’ arrival in 1620, making it one of the oldest towns in the United States. Living in Plymouth offers a unique experience, where residents are immersed in a rich history while enjoying modern amenities and a relaxed seaside lifestyle. From exploring iconic landmarks like Plymouth Rock and the Mayflower II to indulging in outdoor adventures along the pristine beaches and lush trails, there is never a shortage of things to do in Plymouth. So whether you’re searching for apartments for rent in Plymouth or homes for sale, read on for a Redfin guide on fun things to do in your new city.

Plymouth harbor

1. Start your journey at Plymouth Rock

Exploring Plymouth Rock is a fun thing to do when living in Plymouth. This iconic symbol of American history holds a captivating allure, allowing visitors to connect with the Pilgrims’ arrival in 1620 and the founding of the Plymouth Colony. Standing in front of this monumental rock evokes a sense of awe and wonder, as one can imagine the challenges and triumphs experienced by those early settlers. Additionally, the surrounding area offers numerous attractions to enhance the experience. Visit the nearby Pilgrim Hall Museum, which houses an extensive collection of artifacts and exhibits detailing the pilgrims’ journey.

2. Take a stroll along Plymouth Harbor

The harbor offers a picturesque setting with its serene waters, charming marinas, and bustling waterfront atmosphere. Whether strolling along the promenade or renting a kayak, you can immerse yourself in the harbor’s beauty while enjoying various recreational activities. For nature enthusiasts, a harbor cruise provides an excellent opportunity to spot diverse marine life, including seals and seabirds, and learn about the area’s rich maritime history. The harbor is also home to several fantastic seafood restaurants where visitors can savor freshly caught lobster, clams, and other delectable dishes while savoring the pleasant waterfront views.

The Mayflower in Plymouth Getty

3. Step aboard the Mayflower II

For newcomers to Plymouth, exploring the Mayflower is an immersive experience that brings history to life. The Mayflower II is a meticulously crafted replica of the original ship that transported the Pilgrims to the New World in 1620. As you walk the weathered decks and venture below, you’ll gain a profound appreciation for the hardships and resilience of the Pilgrims during their voyage. Engage with knowledgeable guides who share intriguing stories and insights, offering a glimpse into the daily lives of those early settlers.

4. Make your way to the Myles Standish State Forest

Myles Standish State Forest in Plymouth is a  vast natural oasis spanning over 12,000 acres, encompassing serene lakes, lush forests, and winding trails, making it an ideal destination for outdoor enthusiasts. Upon arrival, visitors are greeted by the refreshing scent of pine trees and the soothing sounds of nature. The forest provides many recreational activities, such as hiking, biking, horseback riding, fishing, and camping. Traverse the well-maintained trails, allowing yourself to get lost in the beauty of the surroundings, or embark on a serene kayak or canoe ride along one of the picturesque lakes.

Long beach Plymouth, MA

5. Spend a day at Plymouth Long Beach

Visiting Plymouth Long Beach in Plymouth is a great coastal experience that offers a perfect blend of relaxation, recreation, and natural beauty. Begin your visit by strolling along the pristine sandy shoreline, feeling the soft sand beneath your feet, and enjoying the refreshing ocean breeze. The beach stretches for miles, providing ample space for sunbathing, picnicking, and building sandcastles. Enjoy a refreshing swim in the clear, blue waters or try various water sports like paddleboarding, kayaking, or even surfing, as the beach offers favorable conditions for beginners and enthusiasts alike.

6. Visit the Plymouth Center for the Arts 

The Plymouth Center for the Arts is a vibrant cultural hub that serves as a platform for local and regional artists to showcase their talent. The center hosts diverse art exhibitions featuring various mediums such as painting, sculpture, photography, and mixed media. Visitors can immerse themselves in the art world, exploring thought-provoking and visually captivating works that reflect the artists’ unique perspectives. 

Farmers market in Plymouth, MA

7. Explore the Plymouth Farmers Market

Wandering through the Plymouth Farmers Market is a fun activity that showcases the vibrant local community. As you enter the market, you’ll be greeted by a bustling atmosphere filled with the enticing aromas of fresh produce, artisanal goods, and delectable treats. The market is a treasure trove of locally grown fruits and vegetables, homemade jams and preserves, artisan cheeses, baked goods, flowers, and much more. 

8. Immerse yourself at the Plimoth Patuxet

The Plimoth Patuxet provides a unique opportunity to step back in time and experience firsthand the daily life, customs, and traditions of the 17th century. Engage with costumed interpreters who portray Pilgrims and Wampanoag people, gaining insights into their respective cultures, trades, and ways of life. Take time and explore the meticulously recreated 17th-century English village. It is complete with thatched-roof houses, gardens, and workshops to get a sense of the challenges and triumphs faced by the early settlers.

Humpback whale in Plymouth

9. Embark on a whale watching trip

Plymouth is renowned for its abundant whale populations, including humpback whales, finback whales, and even the majestic North Atlantic right whale. As you scan the horizon, keep your eyes peeled for the telltale signs of their presence—spouts, breaches, and flukes emerging from the water. When you spot a whale, time seems to stand still as you witness their graceful movements and colossal size up close. The thrill of seeing these majestic creatures in person, they’re gentle giants of the sea, leaves an indelible mark on your memory. In addition to whales, it’s common to encounter other marine life, such as dolphins, seals, and various seabirds, adding to the excitement of the experience.

10. Go wine tasting at Plymouth Bay Winery

Plymouth is home to several wineries and vineyards that offer unique tasting experiences, showcasing a variety of locally produced wines. One such destination is the Plymouth Bay Winery, where visitors can sample fruit wines made from locally sourced cranberries, blueberries, and other fruits. The winery’s cozy and inviting atmosphere and the friendly and knowledgeable staff create a memorable experience for wine enthusiasts of all levels. Another must-visit spot is the 1620 Winery & Wine Bar in the heart of historic Plymouth. Here, guests can enjoy tastings of award-winning wines crafted from premium California grapes while taking in the ambiance of the elegant wine bar.

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