Plymouth at 400: a local’s guide to the perfect weekend

In 2020 Plymouth commemorates 400 years since the landing of the Pilgrims. The town is excited to welcome visitors from all over the world, but also from Massachusetts as this is one of the best day trips from Boston!

Hydrangeas in Depot Square, Plymouth, MA

Plymouth is just 40 miles from Boston but it’s a world away. There’s something for everyone in Plymouth- a quintessential beach town with significant history and a lively art scene. All the benefits of a Cape Cod town without the bridge traffic!

We’ve had so many guests since we moved here, that we put together this local’s guide to things to do in Plymouth. Hope you’ll find something you like!

This post includes affiliate links. We may get paid if you buy something or take an action after clicking on one of these. Traveling Tulls is not affiliated with any of the restaurants, hotels, and attractions listed, and has not received any products, services, or fees for this post. All opinions are our own. DISCLOSURE

What to Do in Plymouth, MA

A dog's eye view of Plymouth history

History is Everywhere in Plymouth

In 1620 the Pilgrims, the first group of families to immigrate to the New World, settled in Plymouth. The Pilgrims left England for Holland seeking religious freedom. They settled in the town of Leiden where they lived for about 11 years, before deciding to make the journey to the New World.

Read more about the Pilgrims, their struggles, and their journey

The 400th anniversary of the Pilgrim’s landing is being celebrated in 2020 and 2021 (due to the pandemic). For a schedule of events, visit Plymouth 400.

Plimoth Patuxet (previously known as Plimoth Plantation) draws most of the history buffs. It is a living history museum where you can chat with interpreters playing the parts of the Pilgrims and the local Native American people, the Wampanoag. Plimoth Patuxet is located on Warren Avenue (rt 3A) or can be reached from Rt 3, exit 4.
Admission packages are available that include the Mayflower II ship and, on weekends, the Plimoth Grist Mill. Massachusetts residents should check with their local library as many carry discount tickets to Plimoth Patuxet.

Downtown Plymouth is filled with history. This is, in fact, where the original Plymouth colony was built, and the Pilgrims lived.

A visit to the Pilgrim Hall Museum is a must-do, as is a stroll along the waterfront. Try one of the two walking tours we’ve outlined below if you enjoy exploring history on foot.

Plymouth's Long Beach at sunset

Outdoor Things to Do in Plymouth

Outdoor enthusiasts have more options than they’ll have time to enjoy –

  • Beach lovers – head to Long Beach, a 3 mile barrier beach. During the summer season, beach parking is by sticker only, but the Plymouth shuttle stops at the beach entrance. Food and restrooms are available at the beach.
  • Families with preschoolers will love Nelson Beach Park with its playground, sprinkler park, and protected beach. At the end of the Nelson Beach parking lot is a lovely one mile walking/bike path that everyone will enjoy. This is also where you’ll find the Grace Trail – a meditative walking path.
  • Myles Standish State Forest, a 12,000 acre park, has 13 miles of hiking and bike trails, as well as lakes and ponds for swimmers. Campsites on the crystal clear lakes are in demand so book early if you’re interested! For more cycling suggestions in the area, read Most Beautiful Cycling Paths in Southeastern New England.
  • Tidmarsh Wildlife Sanctuary (Beaver Dam Road) is Mass Audubon’s newest wildlife preserve. 481 acres of ponds, woods, and walking trails. From their website – “Once a working cranberry farm, this landscape underwent the largest freshwater ecological restoration ever completed in the Northeast.” Fascinating to watch the land return to a natural state!
  • Golfers will have their pick of courses to enjoy. Check out the Pinehills Golf Club with its Nicklaus and Jones courses.

Get on the water. Plymouth Harbor is too pretty to skip!

  • Go on a Whale Watching Cruise – Captain John Boats on the town wharf will take you out for a day on the water. Fun for all ages!
  • The Pilgrim Belle is a classic paddleboat that offers a day and evening harbor cruises.
  • Youngsters of all ages might enjoy a Pirate Cruise. Kids dress up, play games, and MIGHT even be called on to fight a pirate ship!!!

Art, Theater and Music in Plymouth

For such a small town, Plymouth has a surprisingly active cultural scene. Live music can be found at many of the local restaurants and bars. Outdoor concerts are a weekly event on the waterfront, and the Plymouth Center for the Arts, on North Street, is a great little (getting bigger!) art museum.

Check out the schedule for Court Streets’ Memorial Hall or Spire Center as they offer traditional and popular concerts. The Plymouth Philharmonic puts on some wonderful concerts throughout the year.

The Plimoth Cinema, located within the visitor’s center of Plimoth Patuxet, shows art, foreign, and well reviewed first run films. And they serve wine on Saturday nights!

Last, but certainly not least, is our summer stock theater, the Priscilla Beach theater. The show barn, where once Paul Newman and Rob Reiner starred, has been renovated, but still has the smell and ambiance of old barn. This is summer stock, so performances may vary, but we have never been disappointed. We are season ticket holders and highly encourage you to try a show if you’re able to get tickets!


Map of walking routes in Plymouth

Walking Plymouth History

Like most New England cities and town, Plymouth has meandering roads, and streets that change names. The main street going through town is state route 3A which begins at the Kingston town line as Court Street, becomes Main Street, then Sandwich Street, Warren Avenue, and finally State Road. Note that these walking tours are both focused around 3A, but the street names may vary. Sorry for the confusion!

Plymouth is a small town and easy explored on foot. I am outlining two options for walking the town: a 2 mile easy walk which circles the downtown and waterfront area, and a 3.5 mile walk (with some challenging hills) that expands on the downtown area. For either walking tour, I suggest you park at the south end of town in the Jenney Pond/Plimoth Grist Mill parking lot (Spring Lane off Summer Street). Many of the locations can be entered for a fee, but just walking the town is still one of the best free things to do in Plymouth.

Plimoth Grist Mill at Jenney Pond

First stop: The Plimoth Grist Mill is a working reproduction of the 1636 grist mill, and is open to visitors Saturday, Sunday, and holidays. (admission included in the Plimoth Patuxet Weekend Heritage Pass which also includes the Mayflower II and the Plimoth Patuxet living history museum)

Historic Homes Options: it’s worth a short detour to visit the two most historical houses in Plymouth-

Before heading down the Town Brook path, walk back up Spring Lane to the Richard Sparrow House – the home sits on Summer Street, just at the entryway into the Jenney Pond/Plimoth Grist Mill area. It is the oldest surviving house in Plymouth, built in 1640 by the English surveyor, Richard Sparrow.

Jabez Howland House – the only remaining Pilgrim house in Plymouth. To visit this home take the Town Brook path past the Grist Mill.
Just before you walk beneath the first overpass, you will see a path leading up to Sandwich St.
Take a right on Sandwich and an immediate right on Pleasant St. to the Plymouth Town Green. This was a muster field for the militia of Plymouth and here you will find the Civil War monument dedicated to those lost during this war and the war of 1812.
Walk through the park, take a left on Sandwich Street and you will come to the Jabez Howland House, built ~1665.
Continue down Sandwich St. to reconnect with the walking route.

Continue behind the Grist Mill onto the paved path that runs along Town Brook. If you’re visiting in April or early May, you might catch the annual herring migration up the brook. The fish will densely pack the brook, before climbing the fish ladder, and swimming off towards where they’ll spawn in Billington Sea, a freshwater pond just a mile upriver.

Following the Town Brook to the end brings you to Brewster Gardens, once the garden plot of the Elder William Brewster. The availability of fresh water from the brook was what led the Pilgrims to settle in this spot. For today’s visitors, the garden is a lovely green space with several interesting statues, a picturesque bridge, and a trellis that is a favorite for wedding photos!

Statue of William Bradford, governor of Plymouth Colony
William Bradford, Governor of Plymouth Colony

You are now on Water Street and in for a treat. Cross the road, turn left, and stroll along the waterfront where you might chance upon an open-air concert, a street festival, or just a lot of tourists enjoying the day. Your walk will lead you to Pilgrim Memorial State Park where you’ll find Plymouth Rock, and the Mayflower II, a full sized replica of the ship that carried the Pilgrims to America.

Did you know? The Mayflower II was built in Brixham, England and funded by private donations. It represented the alliance between the UK and US for collaboration during WW2. The ship has just recently returned to Plymouth after multiple year long restoration in Mystic, CT.

Mayflower 2 ship is one of the most popular things to see in Plymouth

On the same pier (the Frazier State Pier) you will find several excursion boats and the fast ferry to Provincetown. Keep walking along Water Street or stop to explore the many tourist shops, restaurants, and ice cream stores line the harbor.

Two Mile Walk option: take a left on Memorial Drive after the Hedge House, home of the Plymouth Antiquarian Society. Continue to Court Street where you will turn left and enjoy ‘downtown’ Plymouth.
Jump ahead to see what comes next.

All other walkers will follow the waterfront to the town pier and a series of great seafood restaurants. (see below for our favorites) Across Water Street from the waterfront is a charming grouping of shops and restaurants (including our favorite ice cream shop – Peaceful Meadows!) It’s up to you how to explore here – walk the breakwater out into the harbor, have a picnic in the small green space, or continue on along Water Street until you get to Lothrop Street.

Follow Lothrop Street inland, cross Court Street at the crosswalk, and take Allerton Street up (and up) the hill to the National Monument to the Forefathers. This monument is featured in the film, Monumental.

National Monument to the Forefathers: the largest solid granite monument in the US.

Fun fact: though this monument is the largest solid granite monument in the U.S., it was originally planned to be twice as tall. Funding problems, in part because of the Civil War, caused the change in scale and the move to the relatively obscure location on Allerton St.

Continue down Allerton St. until you get to Samoset Street. You can take a left here and walk one block to Court Street or avoid the busy road by continuing across on Allerton to the next left on Vernon St. Take a right on Court Street.

Pilgrim Hall Museum is up ahead on the left. The museum opened in 1820, and is the oldest continuously operated museum in the U.S. The museum features artifacts of the original Pilgrim colony and also focuses on the people who inhabited the area for 10,000 years before the arrival of the Pilgrims – the Wampanoag.

Continue down Court Street, past the 1820 Courthouse, (where the road become Main St.) and take a left on North Street. This brings you into the Plymouth Historical district. Visit the newly redone Plymouth Center for the Arts, admire the Mayflower Society house, and bear right on Carver Street to take in a beautiful view of the harbor on the top of Coles Hill. Here you will also find the statue of Massasoit, and the monument to the original burying place of the Pilgrims.

The road circles around and joins Leyden Street, the oldest continuously occupied street in the US. Take note of the date boards on each of the homes as you head back towards Main Street.

Some of Plymouth’s most popular restaurants are in this area of Main Street, so this might be a good place to take a break, See our recommendations below.

Cross Main Street heading toward the impressive stone meetinghouse, now the National Pilgrim Memorial Meetinghouse on Town Square.

View from Burial Hill in Plymouth

You are now at the base of Burial Hill. I strongly encourage you to climb the steps into the old cemetery. The headstones and the history is surely worth the walk, but the view from the top will take your breath away! The left (southern) end of the cemetery leads to a long driveway that’ll take you back to your starting point – the Plimoth Grist Mill and your car.


Where to Eat in Plymouth

Plymouth has a great variety of restaurants, many featuring live music. Our favorites:

Fine dining in town- Mallebar Brasserie (15 Main St. Extension) – a french bistro with excellent food well presented.

Fine dining – Rye Tavern (517 Old Sandwich Road) – good “farm to table” meals in a 1770 tavern.

Sit-down restaurant on the water – Surfside Smokehouse (14 Union St.). Featuring barbecue and seafood options. You’ll enjoy eating on the covered deck with a view of Plymouth Rock and the Mayflower II.

Best seafood counter style spots – a tie – Woods Seafood and the Lobster Hut. Both located on the Town Wharf and both offer cafeteria style ordering, and seating. Lobster Hut has more extensive outdoor seating on the water.

Other favorites –

  • Martini’s (50 Court St.) has live jazz on Tuesday nights. The foods great too!
  • KKatie‘s Bar (38 Main St. Extension) Best hamburgers around (and get the loaded fries) Helpful hint: order the small burger or split a regular one.
  • Sam Diego‘s (51 Main St.) get points for ambiance. It’s in a renovated fire station with brick walls, big windows, and a gorgeous staircase. Nice place to have a drink.
  • Café Strega (16 Main St. Extension) is popular with locals. Good Italian food and a great view if you get to sit by the window.
  • Blue-Eyed Crab (170 Water St.) has fantastic Caribbean style seafood. Try to get a table outside as it can be noisy inside.
  • For a different outdoor experience, drive to the Stack Shack behind Cordage Park Circle. Sit on picnic tables beside the last remnant of the Plymouth Cordage Factory – a 220 foot smokestack – and enjoy a drink and some tasty, if simple, food.
  • Best pizza? Mamma Mia‘s on the waterfront! (122 Water St.)
Plymouth waterfront has a lively touristy area.

Where to Stay in Plymouth

Note: as residents of Plymouth, we have not stayed at any of the hotels and inns below. Our opinions are based on recommendations by family and friends.

There are several national brand hotels on the outskirts of town – Hampton Inn, Hilton Garden Inn, Fairfield Inn, to name a few. All well maintained and with plenty of parking.

Downtown Plymouth recommendations:

  • Hotel 1620 (180 Water St.)
  • John Carver Inn and Suites (25 Summer St.)
  • By the Sea B&B (22 Winslow St.) – a personal favorite though we’ve never stayed here. The B&B is just charming, with lush gardens and a wrap around porch overlooking the harbor.

A few miles away from the downtown area is the Mirbeau Inn & Spa (35 Landmark Dr.). This is a lovely spot for a romantic getaway, with fireplaces in many rooms, and a replica of Monet’s garden in the courtyard.
This is located in the Pinehills area of Plymouth which boasts two ranked golf courses, and a quaint village center with shopping and restaurants.

Town pier in Plymouth Massachusetts

When’s the Best Time to Visit Plymouth?

As a happy resident of Plymouth, I’d love to say it’s great in any season, but winter in Massachusetts can be difficult. And many of Plymouth’s top attractions are closed for the winter season. Plimoth Patuxet closes after Thanksgiving, and much of the rest of the tourist attractions close then or shortly after the holiday season.

Plan your visit when the weather improves in New England. Spring and Fall are gorgeous, and summer is a perfect time if you’re hoping to enjoy the beaches or get on the water.

Special Days in Plymouth

Independence Day, July 4th.
One of our favorite days of the year! Water St., the harbor front road, is closed to traffic. The celebration begins quietly with a road race in the early morning, then the crowds begin to gather. Plymouth hosts a parade with all the favorites -bands, floats, and firetrucks! Everyone is wearing their red, white, and blue.

In the early evening the Plymouth Philharmonic presents an open air, patriotic concert (get there early for a seat on Cobb’s Hill!) which is followed by fireworks on the harbor.

America’s Hometown Thanksgiving
With Plymouth being the site of the first Thanksgiving, it is fitting that we put on a week long party to celebrate each November. We host the SECOND biggest Thanksgiving Parade and draw crowds from all over to enjoy our hometown spirit. But note: the celebration takes place BEFORE Thanksgiving – usually the weekend before the holiday.

The parade features the history of the town, with replicas of the Mayflower, Pilgrim homes, and, of course, a turkey. Enjoy the parade, but don’t miss some of the other quieter attractions on the waterfront. A historic village is set up in Brewster Gardens; there’s a Wampanoag educational pavilion, and a beer and wine garden, a concert by the Philharmonic, and lots more to enjoy.
Check out the calendar of events before planning your visit. You might even want to make a reservation for Thanksgiving dinner at Plimoth Patuxet!

Getting to Plymouth from Boston

By Public Transportation: the Kingston/Plymouth Commuter Rail (MBTA) leaves South Station in Boston. Either destination is fine for the Plymouth visitor as both will likely require a taxi or an uber to take you from the station to the town center.
It is possible to walk (or cycle) the one mile Seaside/Nelson Park trail to town from the Plymouth station.

By Car: Head South on Route 3 towards Cape Cod. The town center is off exit 6, Plimoth Patuxet is off exit 4, and other Plymouth beaches and destination extend all the way to exit 2.

Parking in Plymouth

Plymouth has a pay parking policy during the busy season – March to November. Several large lots can be found near the waterfront on Water St., and there’s a new parking garage on S. Russell Street next to the Town Hall.

On-street parking is an option if you’re lucky. And if you’re up for a walk, and want to avoid paying for parking, try the lot near the Jenney Grist Mill (Spring Lane off Summer Street) or the lots at the northern end of Water Street near, and including, Nelson Park.

Learn More About Plymouth: Reading and Movie Suggestions

American Experience: the Pilgrims (Amazon Prime video)

Monumental: In Search of America’s National Treasure (film)
90-minute true story follows a man across Europe and the U.S. as he seeks to discover America’s true “national treasure” – the people, places, and principles that made America what it is today.

Mayflower: a story of courage, community, and war by Nathaniel Philbrick (book)

Making Haste From Babylon: the Mayflower Pilgrims and their world: a new history by Nick Bunker (book)

This Land Is Their Land: The Wampanoag Indians, Plymouth Colony, and the Troubled History of Thanksgiving by David J. Silverman (book)

The Plimoth Patuxet gift shop has a wide selection of books for all ages. Definitely worth a visit to find some great titles. And you don’t need to purchase a museum entry to shop the store.


Plymouth at 400: a local's guide to the perfect New England getaway. #plymouth400 #staycation
What to do in Plymouth, MA. An easy daytrip from Boston, or a great New England getaway weekend. #travelNewEngland #pilgrims #coastalMassachusetts #plymouthma #plymouth400
Mayflower 2 in Plymouth harbor. What to do in Plymouth on a daytrip of a weekend getaway from Boston. #coastalnewengland #historicplymouth #plymouth400

6 thoughts on “Plymouth at 400: a local’s guide to the perfect weekend

  1. This looks like a perfect trip for me! I absolutely love history so I would have no problem spending a couple of days here a visiting these spots along with the walking tours 🙂 Hopefully I can once borders are open again!

  2. I’ve been to Boston before but never to Plymouth! I’d love to check out the wildlife sanctuary and the beach there! <3! I miss traveling so much.

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