Plymouth harbor pic

Plymouth, Massachusetts is nicknamed “America’s Hometown.” As most of you already know, the city is most known as being the location of the first Thanksgiving Feast. The city was established in 1620, making it the oldest town in New England, and one of the oldest in the U.S. On our first visit to the area, we found out that Leyden Street is the oldest continuously inhabited street in the country. However, there is much more to this historical area including a gorgeous state park on the waterfront, plentiful outdoor recreation, year-round events, as well as fun seasonal activities.

Tourists flock to this area each year to visit the many historical sites. Pilgrim Memorial State Park, home to Plymouth Rock and the Mayflower replica, is one of the most visited parks in the country (over 1 million per year according to the park website). With so much to see and do, this historic coastal town is worthy of a daytrip from Boston for sure in my opinion. I have been visiting this city for well over a decade now as my sister is a long time resident of nearby Middleboro.

Mike and I moved to the Providence metro several years ago and have been exploring nearly every weekend. As this wonderful coastal city is an easy 30 min drive from where we live in Fall River, we had the wonderful opportunity to explore the various historical attractions and scenery throughout the seasons. In my guide, I will highlight what I think are the must-do activities for first time tourists.

1. Take a Whale Watching Tour

Whale Watching in Plymouth, MA

A Whale Watching tour is my number 1 must-do when visiting this beautiful city. Massachusetts is one of the best places in the world to see humpback whales, so I recommend taking this opportunity while you are here. My experience aboard the Captain John Boat Tour was both fun and educational. This really is a fantastic tour.

Our guide conveniently pointed out the whales and made sure everyone on the boat got a fantastic view. Get your camera ready for up close sightings, as well as fabulous views of the ocean and even a historic lighthouse along the way. Sightings are guaranteed, so don’t worry, you get to come back for free on the rare occasion that you see nothing (don’t worry – we saw more than a dozen!).

2. Take a self-guided tour of historical sites

Most of the major historical sites in town are located within walking distance of each other. Park for free in the Burial Hill Cemetery parking lot and start moving! The most iconic sights include: Plymouth Rock, the Mayflower replica, 1st Parish Church, Leyden St., Burial Hill, and The National Monument to the Forefathers (you may have to drive to this one).

The famous rock and Mayflower ship are both located along a 2 mile long path known as the Pilgrim trail at Pilgrim Memorial State Park. There are also a few museums to explore including the Plimoth Patuxet which features a replica of the original Pilgrim colony.

Plymouth Rock in Massachusetts
Plymouth Rock
Mayflower replica in Plymouth, Massachusetts
The Mayflower replica
National Monument to our Forefathers in Plymouth, Massachusetts
National Monument to our Forefathers, the world’s largest solid granite monument
First Parish Church in Plymouth, MA
First Parish Church, est in 1620

If you are a fan of Halloween or just the supernatural in general, I recommend a ghost tour with Plymouth Night Tour. We loved hearing ghost tours and exploring old historical sites at night. You will even get to walk through creepy Burial Hill cemetery at night!

The tour is super fun – you will hear spooky legends about local hauntings and also get to test out EMF ghost hunting equipment! I felt like I was a real life ghost hunter like Zak and the gang on Ghost Adventures. I have always wanted to try my hand at using real equipment (I love anything to do with the paranormal), so this was a really fun experience for me.

Historic Burial Hill in Plymouth MA
Creepy and historic Burial Hill where some of the gravestone are so beat down that they can no longer be read!

3. Take a stroll along the beautiful waterfront

I recommend a scenic stroll along the waterfront for the most incredible vistas of the harbor. I prefer fall and spring over the summer because I can’t stand the heat and also there are fewer tourists this time of year. At the state park, you can visit the historical sites mentioned above, plus Brewster Gardens, the William Bradford statue, and Cole’s Hill Burying Ground (located across from Plymouth Rock).

Plymouth Harbor

Also check out Long Beach if you have the time. It’s 3 miles long, so perfect for a walk and maybe some seaglass hunting (I’ve never found any unfortunately). It’s also popular for swimming and picnicking.

Long Beach in Plymouth

4. Enjoy a seafood lunch or dinner

Not surprisingly, Plymouth is home to an abundance of seafood restaurants. Wood’s Seafood serves fresh, local seafood at an affordable price. As an added advantage, the dining room overlooks the harbor so the view is fabulous. It definitely is the place to go if you are seeking a wonderful waterfront restaurant. Personally, I don’t like seafood. However, Mike and every family member I have taken here have been really impressed. I do love the waterfront scenery and tasty fries!

Lobster at Wood's Seafood in Plymouth

5. Hike or bike at Myles Standish State Forest

Myles Standish is my favorite place to hike & bike in Massachusetts. There are 13 miles of beautiful hiking trails here where you will pass by ponds, cranberry bogs, and beautiful pine trees. I recommend starting with the Reservoir trail (a 2.5 mile loop) which is pretty easy in comparison to the other hikes.

Other recreational opportunities available seasonally include cross country skiing, swimming, canoeing, and picnicking. This park sees little traffic besides a few locals and it’s massive. It’s just such a peaceful place to enjoy nature in one of the country’s most beautiful areas and I love visiting year-round. As you can see in my pics, the park really shines in every single season. Personally, I love leaf peeping here and seeing the colors reflect on the water.

A 4 season oasis: a gorgeous recreational destination throughout the seasons:

Reservoir at Myles Standish
Summer hiking in the pines
Fall bike ride at Myles Standish State Forest
My favorite place for a fall bike ride
Fall foliage at Myles Standish State Forest
Autumn beauty reflected on a pond
Cross country skiing at Myles Standish State Forest in Plymouth, MA
A winter wonderland for snowshoeing

Addresses & Parking Information

  • Captain John’s Tours Whale Watching Tours – 10 Town Wharf
  • Burial Hill & 1st Parish Church – Leyden St.
  • Plymouth Rock & Mayflower II replica – Water St.
  • National Monument to the Forefathers – Allerton St.
  • Waterfront/Pilgrim Memorial Park – Water St.
  • Wood’s Seafood -15 Town Wharf  
  • Myles Standish State Forest – 194 Cranberry Rd  Carver

*There are parking meters all over town or you can park for free in the Burial Hill parking lot located at: Leyden St. This lot is only 2-3 blocks away from most waterfront attractions.