No visit to Plymouth harbor is ever complete without visiting Cup Cake Charlies. Some of the best
cup cakes we’ve ever had. Take a look at their menu, they have a wide range of cupcakes, cakes, ice cream, whoop cakes,
cookies, etc.
Click here to visit their website.

Plymouth Massachusetts & Vicinity Map

Plymouth county was created in 1685. As of the 2010 census, the population was almost half a million and it is the third largest county in Massachusetts by total area. It’s 434 square miles and includes about 42 towns and cities stretching from Hingham to Plymouth and south east to almost the Cape Cod Canal.
Plymouth Colony is one of the first American colonies (1620) preceded by only a few other colonies such as Roanoke (1585), Jamestown (1607), and St. Augustine (1565). The colonial architectural influence in Plymouth is present throughout the town. As I walked from my brothers house, which was built in 1860, down to Plymouth Harbor I wandered by a home that was built in approximately 1664. It’s hard to find buildings this old in the United States and I stopped to appreciate the significance and to think about what life might have been like during that time in the town.
The images above show a home we walked by on our way to downtown Plymouth, which was built circa 1664, The other images show my brother’s home which was built in 1860 and has been featured in the local newspaper a few times and opened for a Christmas tour of homes on occasion. When viewing the house from the outside the narrowness of the building strikes me. His home contains two apartments and I love the courtyard in the backyard.
Plymouth provides picturesque views on a clear day and the harbor is typically filled with boats of all types. On the northwest side of the bay, Gurnet Point is located at the end of the peninsula that juts out at the entrance to Plymouth Bay. On the southeast side of the bay, there is another peninsula that is about 5 miles long and provides additional protection to Plymouth harbor making it calm on most days. Long beach is located on that peninsula and those looking for a long walk away from the crowds might consider it. Dogs are allowed on leash.
Plymouth Rock is located at the harbor front along with the Mayflower when it is in port. The harbor front street, called Waterstreet, is lined with shops and restaurants. You can pick up your t-shirts, trinkets and homemade fudge in any number of stores. There is a walking path along the waterfront with benches and places to lounge that are perfect for eating ice cream or that homemade fudge that you just purchased.

Cupcake Charlie's

Tavern on the Wharf
They have outside seating with options ranging from Salads to fish tacos and sandwiches to
lobster mac and cheese. We enjoyed everything we tried including the artichoke spinach
appetizer which was perfect for our group of six.
Click here to visit their website.

Lobster Hut
We were looking for outside seating due to
COVID-19 and the lobster hut provides that in the back of the restaurant (faces the harbor). You order
at the counter and find your table. When the food is ready, they call your number.
Click here to visit their website.
One of our favorite day trips from Plymouth is going to Provincetown by Ferry. Taking the ferry to Provincetown is easy and so much fun! The boats have comfortable seating in a climate-controlled cabin with full galley service and great views of historic Plymouth Harbor and Cape Cod Bay. On our trip we saw a few whales which was an unexpected bonus.
Getting to Provincetown via a boat is so much more fun than driving there. Driving to Provincetown on State Road 6 is a 76 mile journey versus 26 miles by boat (approximately 90 minute ride). And remember that State Road 6 can get very crowded, with multiple stop lights in the various small villages along the way. Going by boat allows you to see whales and all types of other sea creatures and the occasional beautiful sailboat.
As of September 2020 round trip adult fares are $60. Click here to view their website.
Some Useful Plymouth Area Links & Suggested Things to do or see
Ellisville Harbor State Park is a seaside park with paths down to the waterfront. If you take the dirt road to the park entrance you can follow the wide path down to the water’s edge. The paths are full of poison ivy so be careful. The beach is littered with driftwood and rocks but there is some sand so you can lay your blanket and spend some time. At low tide you can walk out and go exploring in the rocks and seaweed. Harbor seals swim just off the shore on most days. We rented a VRBO that overlooked the water and had views of the park. Check out the images of the house we stayed in and the stunning views.. Getting to the house was challenging due to the dirt road and large puddles (more like small ponds) but once we were there the views were incredible and we woke each morning to the sound of the seals barking and seagulls crooning.
There are a number of beautiful drives and day trips that you can take from Plymouth. Westport harbor is a small but picturesque harbor. Buzzards Bay Brewing has a Westport location located in the country with an array of beer choices. Stop for a flight to try the different type at a picnic table under the trees.
Canal Railroad Bridge: That bridge weighs 2,200 tons and has a center span of 544 feet. When the bridge was first constructed (completed in 1935) it was the longest vertical lift railroad bridge in the world. The lift section of the bridge is kept in the raised position until a train needs to cross, and then the bridge is lowered, requiring 2.5 minutes to reach the fully lowered and ready position. The bridge is owned, operated and maintained by the US Army Corps of Engineers.
Canal Automobile Bridges: There are two auto only bridges, the Sagamore Bridge and the Bourne Bridge. Construction started in 1933 and was completed in 1935. These bridges were Public Works Administration projects for the US Army Corps of Engineers, who owns, operates and maintains both bridges.
The village of Bourne is another nice drive from Plymouth and sits along the mainland side of the Cape Cod Canal. There is a walking and bike path along the canal, plentiful parking and benches for taking in the view of the Canal Railroad Bridge. We stopped and got some cider donuts and a coffee and sat in the park to take in the views.
Because Sandwich is such a pretty village, adjacent to the Cape Cod Canal and it's eastern terminus and contains
some nice restaurants - we wound up driving here several times for meals and explorations! Our first trek here, we
ate at
The Pilot House Restaurant & Lounge - good service,
good food and great views. On our next visit, we ate lunch at the
Fishermen's View Seafood Market & Restaurant - fantastic
view of the marina and the food was excellent.
Both of these restaurants are within a short walk of the Cape Cod Canal as well as the Marina. A nice way to walk off
a good lunch and watch canal traffic move back & forth.
Deming Jarves founded the Boston & Sandwich Glass Factory in 1825. Sandwich had proximity to a shallow harbor, was a possible canal site, and had local supplies of timber to fuel the glass furnaces. The glass works primarily made lead glass and was known for its use of color. Jarves received several patents for his improvements in glass mold designs and pressing techniques. The factory declined after the American Civil War due to competition from Ohio, Pennsylvania, and West Virginia companies that produced less expensive pressed soda-lime glass tableware.
The Sandwich boardwalk is a popular place to visit in Sandwich. The boardwalk stretches across the marsh to a
beach on the other side. During high tide people jump off of the boardwalk into the beautifully clear water.
You can swim, walk, kayak or just relax. Beware that the daily parking rate is twenty dollars as of 2020.
Click here to
view a great list of images of the Sandwich Boardwalk on Google.
Falmouth and Woods Hole are also a short drive from Plymouth. Falmouth has a quaint downtown area with a number of shops and restaurants. Click here to visit a page with a list of all the shops & places that you can visit on Main Street.
Falmouth has a number of beaches and Woods Hole has a science aquarium that is worth a visit. You can take a ferry to Martha’s Vineyard from here or you can visit Nobska Point Lighthouse or bike along the shining sea parkway.

Since it was lunch time when we started our Main Street exploration, we decided to stop for lunch at Liam Maguire's Irish Pub. They have a nice menu, a pretty good beer list and a nice area in the back with picnic benches and umbrellas. We had a wide variety of food, and everyone agreed that it was tasty!
Take a look at their Yelp listing and the menu, to see why we thought it was a nice lunch stop.
Wellfleet is actually on Cape Cod and is pretty close to Provincetown. If you drive to Wellfleet from Plymouth try to avoid peak tourist time. There are a number of beaches here. If you decide to go for a swim beware that there are sharks in the area.
We met my sister & her husband for lunch at the Bookstore & Restaurant (image #2 above) where we had mussels and french fries. Image #1 and #3 are of the harbor & beach area directly aross the street from the restaurant.
Take a look at the restaurants Yelp Page to see their menu and various reviews.
In our zeal to get to Wellfleet in time to meet my sister & her husband for lunch, we got there way too early and decided to drive up through Truro where we saw the sign for the National Seashore & Lighthouse. Since it seemed to be such a great way to spend some time, we parked and began our exploration. Unfortunately, the lighthouse was being renovated - but - we did discover an unusual fact about the lighthouse; it's original location (450 feet away) was much closer to the ocean, and was relocated when the Atlantic Ocean continued to cause the cliffs there to erode.
The Highland Light is an active lighthouse on the Cape Cod National Seashore in North Truro, Massachusetts. The current tower was erected in 1857, replacing two earlier towers that had been built in 1797 and 1831. It is the oldest and tallest lighthouse on Cape Cod.
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