Road Trip Guide to Exploring Historic Plymouth, Massachusetts for Mayflower Day

Sep 14, 2024

We’re once again expanding our road trip destinations outside the Midwest, but this time we’re headed East! In honor of Mayflower Day, we’re exploring the history of Plymouth, Massachusetts, landing place of the historic Mayflower ship. Located just south of Boston, this historic town is the site of the first Pilgrim Settlement founded in 1620. This quaint New England town is chock full of coastal activities like whale watching, sailing, and boating as well as plenty of top tier dining and shopping, and of course, historical sites! So, hop in your new car from Classic and let’s hit the road to take a deep dive in American history.

Some of the Must See Mayflower Historic Sites in Plymouth

Alden Family Historic Sites – These historic properties are located in the nearby town of Duxbury, and are now managed by descendants of the Alden Family. First, check out the Alden Homestead Site which contains the archaeological remains of the original house built by John Alden, and the John Alden House and historic museum. Explore the life of the Alden family through historical tours and lectures, take a tour of the house and learn about the history of early American/US origins, take a self guided tour of the properties, or enjoy the Alden Pilgrim Quest guided walk that takes you back in time to the founding days of America! You can even take a nighttime haunted house tour during the fall season.

Burial Hill – This historic cemetery and burial ground marks the site of several Pilgrims, as well as family monuments for early settlers of Plymouth.

Coles Hill – This National Historic Landmark contains the first cemetery used by the Mayflower Pilgrims, and has been owned since 1820 by the Pilgrim Society of preservationists, helping to preserve and document the early history and founding of the US. Some of the monuments and memorial stones here date back to the Tercentenary Celebration of the Pilgrim’s landing, as well as a granite sarcophagus which houses skeletal remains believed to be early Mayflower settlers. The area also has beautiful sweeping views of the water and makes a stunning spot for some sunset viewing.

Harlow Old Fort House Museum – One of the few remaining 17th century buildings, it originally housed the family of settler William Harlow, a farmer, cooper, and town official who also served in the local militia. You can take a guided tour featuring a plethora of hands-on activities and historical facts! Learn about what makes this house a special landmark, see artifacts and antiques from a bygone era, and learn about Early American life in colonial New England. The museum also offers special events throughout the year including historical lectures, special presentations, and holiday seasonal events such as A Christmas Carol.

The Jabez Howland House – This historic home has been preserved, restored, and redecorated with 17th century period furnishings and accoutrement. It’s the only remaining house in existence which housed actual pilgrims, John and Elizabeth Howland and their son, Jabez Howland. You can also visit the nearby John Howland Homestead Site and read a little more about the history of the Howlands.

The Jenney Interpretive Center – Dedicated to sharing the life, times, and significant historical impact on of the 51 Pilgrims who arrived in Plymouth and kickstarted the early founding days of the US. Enjoy walking tours of the historic Plymouth district, tours of National Monument to the Forefathers, and numerous educational lectures and programming.

The Mayflower II and the Mayflower Meetinghouse – The Mayflower 2 was built in England to be a replica of the original 17th century ship that transported the Pilgrims here. The ship is a working vessel and floating classroom, allowing visitors an up-close view of the conditions and journey of the Pilgrims across the Atlantic. The nearby Mayflower meetinghouse stores records from the original Pilgrims and their ancestors, and is currently the 5th structure in this location.

The Mayflower Society House and Colonial Revival Gardens – This stunning 18th century period house museum is operated by the Mayflower Society and contains three centuries of artifacts and historical displays.

And of course, Plymouth Rock itself. Although it is rather unassuming in size, this historical monument is protected along the shores of Plymouth Harbor at the world-famous site where the original Mayflower landed.

Other Fun Activities to Explore in Plymouth, Massachusetts

Once you’re done exploring the depths of early American history and the voyage of the original Pilgrims, you’ll find even more fun and excitement to be had! We highly recommend exploring the downtown area which is jam packed with unique little shops, stores, and eateries at The Shoppes at Village Landing. You can peruse the local shops such as “Locally, Yours” or “Plymouth Harbor Knits” or the “Whimsical Wishes Gift Shop” to take home some commemorative souvenirs and artisan goods. Kick back and relax after all of your touring with a rejuvenating visit to Iris Massage and Esthetics. Grab a bite to eat at Salt, Blue-Eyed Crab Grill & Raw Bar, or take a sip of some fine wines at 1620 Wine Bar.

Expand your horizons outside of historic sites by booking a Harbor Cruise or doing some Whale Watching with the family. Hop on the ferry to take a little jaunt over to the tip of Cape Cod and explore Provincetown.