A Weekend Guide to Plymouth, Massachusetts

Massachusetts is a destination hot spot in the summertime (and basically all the time) and since I’ve been living here for going on sixteen years, I never really understood how lucky I am to be so close to so much history. Plymouth, Massachusetts is a very large town that holds a lot of our history and is essentially America’s hometown, but why would someone want to travel across the country, across the world, to see a rock? 

Either way, my dad finally shed some light on what I feel like wouldn’t be a great trip – the Cape is very close, Boston is a short trip, and you’re right on the water. What could be better? If you’re thinking about making the trip in the future, this weekend guide to Plymouth is for you!

A Weekend Guide to Plymouth, Massachusetts


No matter how you get to Plymouth, you’re going to need access to a car if you want to leave Plymouth whatsoever. If you fly in, get a flight into Boston (Logan International Airport), rent a car, and drive down. The drive from the airport to Plymouth is about an hour, maybe a little more depending on traffic, but it’s an easy drive!

A Weekend Guide to Plymouth, Massachusetts


There are a lot of B&B’s and (basic) hotels in Plymouth, but the By The Sea Bed and Breakfast right on the waterfront is seriously in the best location and it’s adorable! The B&B is owned by the sweetest couple that bought the home in 2000 and renovated it to what it is today. The old charm and close location to Plymouth Harbor make it the perfect destination for a long weekend! 

Other great places to stay during your visit include The Jesse Harlow HouseHotel 1620, and the Seabreeze Inn Bed and Breakfast.

A Weekend Guide to Plymouth, Massachusetts


Whether you want to stay in Plymouth or head into Boston or down the Cape for the day, there is plenty to do. 

White Horse Beach – White Horse Beach has been one of my favorite beaches every since I was little. My mom grew up going to this beach, and she’s been taking me ever since. The beach houses are so quaint and the sand is amazing. I love being able to go to the beach where it is quiet and peaceful and not loud from rambunctious high schoolers.

Plymouth Plantation – A learning experience for both children and adults, Plimouth Plantation is a reenactment of the lives of the Pilgrims when they first landed in Plymouth and the lives of the natives that lived on the land prior. From learning how to build fire and chuck a canoe from a tree trunk, to the animals that live on the property, I promise you that you’ll have an amazing time!

A Weekend in Plymouth, Massachusetts

Mayflower II – I haven’t been on the Mayflower tour since I was a little girl, but it’s a must-do when you visit Plymouth, especially on your first trip! And for any of you that don’t know, the Mayflower II is not the original ship that sailed across the great blue sea (aka the Atlantic Ocean) from England. I hear tourists talk about how amazing it is that the ship has lasted all of these years and I die a little inside every time I hear it.

Spooner House Museum – One of the oldest houses on the street, the Spooner House still has it’s original furnishings from the 200 years that the Spooner family occupied it. Now turned into a museum, the home is now open for seasonal tours and is thought to be haunted.

A Weekend Guide to Plymouth, Massachusetts

SHOP! – There are a lot of cute little stores that you can pop in and out of in downtown Plymouth and they are adorable! If you’re looking to find a piece of classic New England, you are guaranteed to find it in these shops and if you’re looking for a cheesy souvenir, you are beyond guaranteed to find something in these shops. Poke around and find something pretty for yourself.

A Weekend Guide to Plymouth, Massachusetts


The Plymouth Rock – The most “historic” part of Plymouth. THE rock that the Pilgrims first set foot on when they landed in New England to start their lives over. Getting a good shot of the rock can sometimes be hard because of all of the tourists flocking the area, but if you get in at a good time (early evening), you’ll get a great picture with a great background!

A Weekend Guide to Plymouth, Massachusetts


Sam Diego’s – Who doesn’t love a little Mexican food? Sam’s has the best tacos, nachos, and did I mention, watermelon margarita? I’m not usually a margarita fan (judge me), but there’s is too good to pass up and the large (27 oz.) is only $13.

The Cabby Shack – If you come to Plymouth and don’t visit my favorite seafood restaurant, shame on you!! But seriously, try the fried clam strip plate (yum!!) or the shrimp scampi pizza if you’re feeling adventurous. The fish is as good as the drinks, and the mojitos are top notch.

A Weekend Guide to Plymouth, Massachusetts

Blue Blinds Bakery – From tasty pastries, to sandwiches and coffee, the Blue Blinds Bakery has the warmest ambiance to it and the yummiest food to eat! I highly suggest you try a pastry and a cup of coffee before your day of adventures!

A Weekend Guide to Plymouth, Massachusetts

A Weekend Guide to Plymouth, Massachusetts

Talk about cute, right?

The nightlife in Plymouth is also amazing so if you’re looking for a place that you can catch some live music and have a couple drinks, you’re in the right place! Many of the everyday restaurants turn to bars every night, so all you have to do is walk the strip! Some of my favorites are The Cabby Shack, Martini’s, T-Bones, and the Waterfront!

Have you ever been to Plymouth?!


  1. August 24, 2016 / 6:59 AM

    I love here + love to play tourist sometimes! You hit the nail on the head Rachel !

  2. August 24, 2016 / 12:44 PM

    what a cool guide! thanks for this! I’ve never been to MA – I clearly need to go!!

  3. August 24, 2016 / 1:11 PM

    I’m in love with places that have a historical background so I may just need to add Plymouth to my list. I’ve always wanted to go to Salem for the witch trails, and I know it’s less than a 2 hour drive from there so it sounds like a great pit stop to me!

  4. August 28, 2016 / 7:26 PM

    Looks amazing! We have never been to Massachusetts but totally want to go now!!

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