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Fall is an ideal time to visit Plymouth and the South Shore of Massachusetts. Along with the cooler weather and the changing of the leaves comes the common desire to get out and explore. If you’re planning a fall road trip to our little corner of the Commonwealth, let us offer some suggestions of places to visit and activities in the beautiful South Shore region and coastal communities.. 

Embrace Plymouth’s History

Plymouth is renowned for being the site of the first Pilgrim settlement in America, boasting landmarks such as the iconic Plymouth Rock and the Mayflower II. The city, often referred to as “America’s Hometown,” features historical sites such as the Plimoth Patuxet Museums, which attract visitors interested in early American history, maritime history, and New England culture. 

Take a Historic Tour 

Suppose you want to explore historical landmarks further than the Plimoth Patuxet Museums. In that case, you may wish to embark on an unforgettable journey touring the historic streets of Plymouth, Massachusetts, on board our Ms. Vicky’s Plymouth Tour, a cutting-edge, environmentally friendly electric vehicle that travels to 21 locations, revealing captivating narrations that bring each landmark to life. During your tour, you’ll encounter intriguing details surrounding the Pilgrims’ voyage to the New World and explore the challenges that shaped life during the early years of America.

The Pilgrim Hall Museum is a must-visit destination for your fall road trip. The Pilgrim Hall Museum is the oldest continuously operating museum in the country, where visitors can immerse themselves in the 400-year-old story of the Pilgrims and the Native Wampanoag people. Families can enjoy daily Treasure Hunts for all ages every public day at Pilgrim Hall – and there’s plenty for grown-ups to explore, too, in this unique historic destination. The 2025 Season Hours are Wednesday through Sunday, from April 2 to December 6, from 9:30 am to 5 pm, with last admission at 4:30 pm.

Explore the South Shore Irish Heritage Trail 

Take a journey through nine scenic towns in coastal Massachusetts on the South Shore Irish Heritage Trail. From Weymouth to Plymouth, you will see places where the Irish lived, worked and built new lives in a country far distant from their homeland. It makes for a pleasant drive and day trip where you and your family can explore your heritage or just enjoy the history of the people who once lived there. 

For a more detailed itinerary, explore our blog on planning your South Shore Irish Heritage Trail tour, which includes suggestions for each town along the route. 

Celebrate the Halloween Spirit in Plymouth 

If your road trip is planned for the end of October, consider taking advantage of the seasonal events on the South Shore that focus on Halloween. Plymouth has several events and activities that you and your entire family may enjoy. 

• Wicked Wild Walks of Plymouth is an immersive and interactive walk through history that you will ever encounter. The professional actors on this wicked, wild walk reenact tales from fact to fiction using imaginative improvisation and scripted works. Book your tour now. 
• Dead of Night Ghost Tours takes visitors on a leisurely walk through the historic, haunted district. Choose from two walks where you can hear the history of the region, visit places the spirits haunt, and learn why they haunt Plymouth, MA. 
• Burial Hill Tours provide access to the site, which is one of the first settlers’ forts and the burial place of William Bradford and Mercy Otis Warren, an American historian, poet, and playwright who lived from 1728 to 1814. The Plymouth Antiquarian Society and Pilgrim Hall Museum have collaborated to offer thematic tours of Plymouth’s ancient burying ground to the public on the first Saturday of each month from February through December. 
• Halloween on Main Street and Trunk and Treat are great options if you plan to be in Plymouth on Halloween. ​​Trick-or-treating in Plymouth, Massachusetts, takes place annually on Halloween, October 31st, with various events including the “Halloween on Main Street” walk for downtown merchants and an event at Town Hall. The Plymouth Family Resource Center also hosts its annual Trunk & Treat event for the community, providing another opportunity for families to enjoy Halloween.  
• Haunted Carousel at Paragon Carousel in Hull will offer two options, including a “Boo”tifully Tame Time for younger visitors from 5 pm to 6 pm on October 18th and where the scares get real from 7 pm to 9 pm. 
• Halloween Tea and Tarot at Shelley’s is being offered on October 30th from 5-7 pm, where visitors can have their Tarot cards read and enjoy spooky decor and treats!  

If you or your family plans to take a road trip to Plymouth this fall, explore the See Plymouth Itinerary page or the “Things To Do” sections for inspiration on designing fun and seasonal activities throughout your trip.