Over the years I have had many visits to the peninsula of Cape Cod Massachusetts. I have found some of the best Cape Cod towns to visit that make a perfect road trip this summer. Two of my favorite routes are scenic 6A on the bayside and Route 28 on the East side (ocean side). Route 6 runs inland and is the best way to leave the Cape. The more scenic drive takes you through various towns and quaint areas that scream New England.

The five top towns that are my favorites are Sandwich, Hyannis, Yarmouth, Chatham, and Provincetown. These are the best Cape Cod towns in my opinion you should not miss. Cape Cod can be done in a day for a quick day trip from Boston if that is all the time you have. But I love to spend the night in some towns depending on the timeframe of the trip. This guide is a glimpse into Cape Cod that will create lifetime memories.

These towns are listed in order based on a road trip from Boston. Since you can visit them as you drive thru the Cape and later return on Route 6 to Boston. If all you have is a day. I recommend going extremely early and leave very late to avoid the infamous bridge traffic to and from the Cape. However, I have also suggested some of the best places to stay in Cape Cod.

Sandwich

Sandwich is the oldest settlement/village (town) on the Cape, founded in 1639 (and one of the oldest in the USA).  The historic area I tend to visit is near the historic Daniel Webster Inn started in 1639.  This area is more away from the beach/coast, but has many older buildings that have cafes, small shops and bakery.  It may be a great place to stop at Beth’s Bakery & Cafe or a place like The Brown Jug, to get some coffee and some tasty breakfast treats, sandwiches, pizza, pastries, etc. Sandwich also has some other dining options including at the Daniel Webster Inn, and of course more is open in season. Stop by the lovely mill still turning water on Route 130. After finishing my tasty treat, I head to Cape Cod’s hub of Hyannis.

Find the Best Cape Cod Towns for a road trip this summer in this guide. Also, the best place where to stay in each!

Where to stay in Sandwich, Massachusetts?

Cottage on the Beach– Stay at the beautiful cottage right on the beach in Sandwich for an amazing rate of $174 USD per night.

Belfry Inn and Bistro- Not only is this a beautiful place to stay the restaurant on site is great. I had one of the best burgers ever here and they also have a fine dining option as well.

Hyannis

Hyannis is the largest of the “village” on the Cape. It’s the commercial and transportation hub on the Cape and home of the John F. Kennedy Museum that highlights JFK’s family vacations given the nearby Kennedy Compound in Hyannis Port.  Visitors to the area can also do the self-guided tour called the Kennedy Legacy Trail throughout the downtown area. The port in Hyannis includes ferries to the Islands like Nantucket, as well as deep-sea fishing and dinner cruises. Loved my last catamaran that sailed just before sunset that gave a glimpse of the compound.  

The main street near the museum has various restaurants, including the Common Ground Café, an eco-friendly café with a unique interior, usually a must stop for me.  There are also some great seafood restaurants near the port like Spanky’s Clam Shack, where you can eat and watch boats come in and out of the harbor.  On the main street and throughout the area there are numerous ice cream shops, or if chocolate is your favorite, head to Kilwin’s across from the museum; of course, salt water taffy is a Cape favorite too.  Hyannis can be an area to stay in overnight since it’s centrally located and it has some of the larger brand hotels.

Where to stay in Hyannis, Massachusetts?

DoubleTree By Hilton

Anchor In is a more local family owned hotel and is a distinctive waterfront property in Cape Cod and offers a great stay in Hyannis, Ma.

Yarmouth

As I leave Hyannis, I head out on Route 28 to the area of Yarmouth.  Along this route you will see many more hotels/motels that span the budget from budget friendly to places like The Red Jacket on the waterfront. I have also been drawn to the smaller local waterfront places near this location. This area also has many restaurants like The Pancake Man (South Yarmouth) and fun family things to do like mini-golf, souvenir shops, and of course the beach.

One of my favorite restaurants is the Skipper Chowder House (that reopens for the season May 6), I had an amazing salmon on a salad with strawberries, etc. one of the best I ever had, while sitting on the rooftop deck where you can see the nearby beach across the way. Hearth N’Kettle is another great option.  Besides the larger hotels, you also have some mid-century places like the Surfcomber on that waterfront that I once stayed at during “the season” or the cute little costal cottages that dot the area. I find the area on Rt. 28 running from Hyannis thru Yarmouth has a great variety of things to do, places to stay or eat at for all ages.   

Where to stay in Yarmouth, Massachusetts?

The Inn at Yarmouth Port – Close to museums, galleries, and shops this is a prime spot to relax and enjoy your Cape Cod vacation.

Chatham

Chatham, Massachusetts

Next on my list as I wind thru the various towns on Route 28 is Chatham.  The village of Chatham is quaint and the posh at the same time. The cute Main Street is dotted with churches, stores and even has the Orpheum Theater. There are many local merchants including sweets, bakery, books shops and art galleries, as well as name brands like Lilly Pulitzer, Fat Face, etc.  Don’t miss the small little places on alley’s, such as the Snowy Owl Expresso Bar that has a nice little area to sit under the shade or grab a cub of joe as you stroll the area. 

There are numerous places to eat, but one of my favorites is the Wayside Inn and the Wild Goose Tavern also on the main street.  You can also go by the harbor for seafood “to go” at the Chatham Pier Fish Market. There are also other options along the waterfront to view the ocean and eat or see the beach. 

Where to stay in Chatham, Massachusetts?

Waterfront at the Chatham Bar Inn.
Chatham Bar Inn has one of the best waterfronts.

Chatham Bars Inn is one of the best inns on Cape Cod with beautiful views and the epitome of luxury on the Cape you cannot go wrong with a stay here.

Captain’s House Inn is perfect for history lovers looking to stay in an old whaling captains home on the Cape.

Provincetown

On the way to see the final town, Provincetown, you may want to stop by the Cape Cod National Seashoreestablished in 1961 by President John F. Kennedy. It stretches over 40 miles of seashore.  Several towns dot the National seashore , but I typically stop to see it in Wellfleet. Wellfleet also has an amazing drive-in theatre. On your way to Provincetown, where the Seashore ultimately ends you will find grand sand dunes. There are various bikes path, beach areas, and birding areas.  After a quick stop there to stretch my legs, I head to Provincetown. The Cape Cod National Seashore extends with its dunes and beaches on the ocean side to your final destination.

There you can swim and have a long walk on the beach, or if adventurous, go four-wheel driving. Later I head to the downtown area that is typically very busy with many tiny streets and alleys like other older fishing villages. On Commercial Street, the main drag, there are many restaurants and places to stay.  Eat dinner at the famous Lobster Pot a landmark restaurant overlooking the Provincetown Harbor. Another favorite is The Squealing Pig gastropub. However, there are numerous great places in the area to have a great bite to eat before you head off Cape or to your hotel. 

This is a summary of some of the top village on Cape Cod. It doesn’t include the multitude of adventures you can find that in my other Cape Cod Guide. Also, there are itineraries that also include Nantucket or Martha’s Vineyard.  But even if you have one day, you can get a good idea of Cape Cod. There is so much history, great food, amazing beaches, it is hard to go wrong. Also, many artists call this home so you will find a creative spirit permeates the entire Cape Cod as you explore the best Cape Cod towns. Whether you have a day or week to visit, this is a must while you are traveling New England.

Where to stay in Provincetown, Massachusetts?

One iconic place to stay in Provincetown, Ma is the historic and luxurious Crowne Pointe Historic Inn and Restaurant.

Sarah Fay in front of the flag house, the best towns in cape cod.

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