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Downtown Plymouth Is The Perfect Seaside Town, But Is It Worth Visiting? This Itinerary Says ‘Yes’

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It made history as the first place of landfall for the pilgrims in 1620, and it’s the perfect balance of modern and (very) historic.

Plymouth, Massachusetts is home to some of the most historical moments in America’s history. It also happens to be a beautiful, sleepy seaside town that’s home to more than a few ways to pass the time. This small New England town is completely walkable and is far quieter than one would expect, with the harbor full of local boats and the famed Plymouth Rock only a short distance away. So, is it worth visiting?

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In short, the answer is yes. Most historical things around Plymouth can be seen in about two days, with the rest of a weekend encompassing its local dining and other activities, such as whale watching. It’s the perfect destination for a long weekend, a great family-friendly place to learn about one of the country’s first settlements, and the Native Americans who called this land home long before that. In Plymouth, it’s not a question of whether it’s worth it, it’s a question of, “when should we go?” And here are all the reasons why.

Where To Stay

It might be small, but Plymouth has no shortage of places to spend the night. Visitors will find anything from historic inns such as the John Carver Inn to cozy bed and breakfasts, many with views of the surrounding town or the harbor.

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There’s never any shortage of accommodations that will make guests feel as though they’ve found a nautical home during their stay, and there’s something intimate and homey about Plymouth’s array of bookings. Perhaps it’s being able to wake up to the sound of seagulls over the water, or knowing you can walk down to the harbor first thing in the morning – either way, it’s magical. No matter where you stay, make sure it’s somewhere in or close to Plymouth’s historic downtown area.

What To Eat

Of course, there’s no shortage of seafood in a coastal New England town like this. Most people will immediately be drawn to the Town Wharf which is just past Water Street around the traffic circle. This entire waterfront area gives way to many dining options, most of which have waterfront views. If you’re staying downtown, these will all be within a five to ten-minute walk. The Lobster Hut is a great place for local seafood at great prices, with some of the best views of the harbor in Plymouth. The food is classic New England-style and the outdoor deck offers the best seating around.

shops in plymouth, ma

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Further back from the harbor along Water Street, visitors will find bar and grill options, a wine bar, and some other diverse dining options, all of which are highly rated for the food and atmosphere. On the opposite side near Pilgrim Memorial State Park, visitors will find pub options and some cafes. After dinner, it’s highly recommended that a visit to Cupcake Charlie’s is in order for some of the best (and most unique) cupcake flavors around. Kilwin’s is also a worthy stop for desserts such as ice cream, fudge, and other treats. For comfort food, Mamma Mia’s is an absolute must – it’s home to some of the best Italian food in the area and also offers harborside views. Near Main Street, visitors can find even more dining options from taverns to breweries and even a winery, and it’s worth exploring if you’re up for a walk – this is a hub for good eats! In the morning, head down to Blue Blinds Bakery, a landmark staple downtown that offers a great cup of coffee and the best pastries around.

What To Do

Explore the waterfront! This is the easiest thing to do and it’s also free unless you’ve signed up for some tours; Plymouth Rock can be seen just past Pilgrim Memorial State Park, which is also worth exploring as it’s fairly small and incredibly scenic. At the end of Frazier State Pier, visitors will find the Mayflower II, which is a nearly exact replica of the original Mayflower that made landfall not far from where its replica sits today.

the mayflower II in plymouth, ma

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Visits to the Massasoit Statue and Pilgrim Mother Fountain are also easy walks from the Mayflower II, with Plymouth Rock in between them and the William Bradford Statue to follow. Right across from this is Coles Hill Burial Ground which serves as the final resting ground for many of the passengers who were on the Mayflower.

plymouth rock in plymouth, ma

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By looping back up Carver Street, visitors will find themselves in the heart of historic downtown, where they can take a guided tour of the Mayflower Society House or sign up for a lantern tour of Plymouth (or a spooky night tour!). The Pilgrim Hall Museum should also be on the list, as it’s the oldest museum in the country and gives guests a detailed, and full, history of what it was like for the earliest settlers coming to America.

inside pilgrim hall museum

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This will bring visitors full-circle back to the same area of the Wharf, just in time to head into the center of the town square and do some shopping at some of Plymouth’s most unique and historic boutique shops. Or, take a queue from the boats entering the harbor and head out for a whale tour (schedules change seasonally).

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