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Plan a Long Weekend in Massachusetts

5 minutes read Jun 17,2021
Plan a Long Weekend in Massachusetts

Massachusetts is home to some of America's most important history. It's also a fantastic place to unwind and relax.

Whether you're the type who wants to explore the coast and plant your toes in the sand, or visit some of America's most important historical sites, The Bay State has it all. If you only have a few days to visit, here's how to make them count.

Day 1: Cape Cod National Seashore

On day one, make your way up US-6 along the Cape Cod National Seashore for breathtaking views of the Atlantic Ocean. There are six beautiful beaches spread out across the peninsula, so you can pick one and plant your toes in the sand, or try to see them all!

If you're the adventurous type, Cape Cod National Seashore is also home to eleven hiking trails, ocean kayaking, and biking. You can even drive off road on some of the beaches if you get a permit.

Race Point Beach can be found at the tip of the peninsula just north of Provincetown. Spend your time near the water or explore the nearby Race Point Lighthouse for stunning views of Cape Cod Bay.

After a long day of adventure, The Lobster Pot is waiting for you near the water in Provincetown. This local favorite offers fresh seafood from the source in a cozy, historic location. Of course, the main attraction is lobster, and there are plenty of ways to enjoy it at The Lobster pot. We recommend the lobster ravioli alfredo and a mug of Tim's Clam Chowder.

Marthas Vineyard Near Cape Cod

Day 2: Martha's Vineyard

On day two, visit one of Massachusetts' most popular destinations: Martha's Vineyard. You'll need to take a ferry to get there, and if you want to take your car with you, the Steamship Authority ferry is the only way to make it happen. You'll want to make a reservation in advance as the spots fill up fast. Once you're on the island, there are countless things to do.

Martha's Vineyard Beaches

There are 19 beaches spread across the island, but some of them are reserved for residents. If you're looking for calmer beaches, the northern and eastern side of the island is your best bet. Our favorite is Oak Bluffs Town Beach near the northwest tip of the island. This beach is open to all and has calm, shallow water -- perfect for a day in the sun.

Martha's Vineyard Food

Believe it or not, there are no chain restaurants on the island. Instead, you can pick from one of the many local establishments serving the best seafood and fresh farm-to-table ingredients. Highlights include ArtCliff diner and its poblano hash, Bill Smith's Martha's Vineyard Clambake Co. for clam bakes, and Ben and Bill's Chocolate Emporium for a scoop of ice cream.

Martha's Vineyard Activities

If laying on the beach isn't your idea of fun, there are countless Martha's Vineyard activities on the island like biking the perimeter, hiking one of the many trails that connect throughout the island or renting a stand-up paddleboard or kayak. Adventure awaits you everywhere!

Downtown Plymouth, MA

Day 3: Plymouth

No trip to Massachusetts would be complete without a trip to Plymouth, home to Plymouth Rock and the very town where pilgrims settled in 1620. There's history in every corner of Plymouth ready for you to explore.

Start at the Plymouth Rock at Pilgrim Memorial State Park, where the monument sits under a stone structure. There's a lot of myth and mystery surrounding the rock itself, and it's been through a lot over the years, but we won't spoil the fun. You'll have to visit and learn about this piece of Americana for yourself.

Next, head over to the Mayflower II, which is a full-scale recreation of the storied ship that carried the pilgrims to North America. Normally, the ship is docked in Plymouth, but it made a special trip up and down the coast in mid-2020. These days, you'll find it docked and ready for a tour. Tours last about an hour and fill up quickly so make sure you buy tickets in advance.

End your day at Tavern on the Wharf, a laid-back eatery right on Plymouth Harbor where you can relax and unwind next to the ocean with some of Plymouth's best local fare.

City of Boston, Massachusetts

Day 4: Boston

On your final day in Massachusetts, make your way up to Boston. There's so much to see in Boston you could spend months here and still not see everything the city has to offer. To help assist you, we've narrowed it down to a few top choices.

First, grab tickets to a historic tour of Fenway Park. The storied ballpark is another slice of Americana and a must-do for any sports fans. Tickets start at $27 per adult.

Next, drop into the Isabella Stewart Gardner Museum. This art gallery is truly one-of-a-kind and was recently featured in a Netflix series titled "This Is a Robbery: The World's Biggest Art Heist." The atrium in the middle of the gallery is unforgettable.

After all that walking, you're going to want to relax and refuel. One of the best places to do that is Samuel Adams Brewery, which is just a few minutes south from the Isabella Stewart Gardner Museum by car. Grab a pint at one of the nation's largest and well-known breweries. You can also join a tour where lunch or dinner is provided if you have beer lovers in your group.

Finally, end your day in the North End, Boston's oldest neighborhood and home to a variety of incredible Italian restaurants as well as Paul Revere's house. We suggest Carmelina's, which is one of the best Italian restaurants the North End has to offer.

Where to stay in Massachusetts

Massachusetts is also home to some of our popular resorts, which are all located conveniently near the destinations on this list. Whether you want to stay close to the ocean at Sun Retreats Dennis Port, be tucked away in the woods at Sun Retreats Cape Cod, or enjoy boating and other outdoor recreation at Sun Retreats Peters Pond, you can't go wrong.

Site and cabin rentals are filling up fast, so book your stay today.

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