Eat New England

Exploring Plymouth, the South Shore Town Beloved by Foodies, History Buffs

This South Shore community has a lot more going for it than being the site of a Pilgrim colony and perhaps the first place to celebrate Thanksgiving.

When you hear the name “Plymouth,” what comes to mind? It may be something related to New England history — and U.S. history, for that matter — as the South Shore town by this name is where the Pilgrims arrived in 1620, which is one reason why the community is often called “America’s Hometown.”

Indeed, those who are into history will have a field day here between the old homes, the museums, the monuments and statues, and yes, Plymouth Rock, which is where the Pilgrims apparently landed. And while tourists from around the world come to Plymouth to see its many historic attractions, both tourists and locals alike can easily overlook the fact that even without its history, this town is one of the most interesting in all of Massachusetts in part because of its scenic beauty, extensive restaurant scene, and abundance of options for outdoor activities.

Plymouth is a huge town, not necessarily population-wise, but in area; at nearly 135 square miles in size, it is actually the largest community in the entire state, and anyone driving from Boston to the Cape can tell you this, as it seems like the stretch of Route 3 that cuts through town goes on forever.

Plymouth Harbor
Marc Hurwitz
Plymouth Harbor / Marc Hurwitz

As you might expect with so much space, Plymouth has a wide variety of landscapes, from the rugged seaside cliffs north of the center to the high hills south of the downtown area and beaches everywhere, while heading west will bring you to one of the most remote-feeling sections of New England in Myles Standish State Forest, which some say has areas that have still never been explored.

Being that this is southeastern Massachusetts, you’ll also find a number of cranberry bogs, which turn particularly beautiful in the fall with their deep reds contrasting with the greens, reds, yellows, and oranges of the trees surrounding them.

It is difficult to know where to start when it comes to describing the restaurant scene in Plymouth. Here you’ll find townie bars, popular pizzerias, upscale and high-end eateries, old-fashioned family restaurants, and, of course, some tremendous seafood spots.

If seafood and views are what you want, a good place to start is the town wharf area where you’ll find such iconic places as the Lobster Hut, Wood’s Seafood, and the Cabby Shack. For those who want a simple meal at good prices, the Lobster Hut or Wood’s Seafood are great options with their chowder, lobster rolls and fried and broiled fish, while the Cabby Shack is where you might want to go if you want a bit of entertainment with your seafood, including trivia night and live music.

Lobster Hut Plymouth
Marc Hurwitz
Lobster Hut / Marc Hurwitz

The waterfront is also home to such local faves as Mamma Mia’s, an Italian restaurant with excellent pizza, the casual upscale East Bay Grille where people dine on regional and New American fare, and Tavern on the Wharf, a dining spot with plenty of seafood while also offering Italian fare and American classics. Plymouth Center is a very short walk up the hill from the water and it has some good food options as well, including The Tasty, a gastropub-style spot that is known in part for its cocktails; Sam Diego’s, a fun eatery that offers Tex-Mex and Southwestern dishes; and KKatie’s, a burger bar with some of the best burgers on the South Shore.

Although much of the rest of Plymouth is residential, commercial/industrial, and undeveloped, a number of other dining spots can be found in the little nooks and crannies away from the waterfront and downtown sections of the community.

One of the most charming is the Rye Tavern, an out-of-the-way restaurant several miles south in The Pinehills area where half the fun is actually trying to find it, with the place being an upscale New American spot with a real colonial feel to it complete with fireplaces, exposed beams, and the like.

A much different experience can be had at Squinny’s, a pizzeria that is also rather difficult to find (it resides in a sprawling area of office parks and industrial buildings west of town) and whose pizza leans a bit toward bar-style (this is the South Shore, after all) while also having some Portuguese touches including a chourico pizza along with kale soup and stuffed quahogs, or “stuffies” with plenty of diced clams.

Marc Hurwitz
Squinny's / Marc Hurwitz

Seafood lovers who might not want to head into the center of town have a good option in Rock Bottom, a no-frills seafood joint in Cedarville, a tiny neighborhood that’s a good distance south of town heading toward the Cape Cod Canal. Here you’ll find stuffies, lobster rangoons, broiled swordfish, fried smelts, popcorn shrimp, steamers, lobster rolls, and lots more from the sea.

In addition to restaurants, Plymouth also has some other food and drink spots that are well worth checking out. One of the best is Cupcake Charlie’s, a dessert shop on the town wharf that features all kinds of cupcakes as well as freshly-made takes on treats from the past, including ring dings, whoopie pies, funny bones, and Hostess-style cupcakes.

If you love Portuguese food and want to stock up, Quintal Brothers Farmer's Market is a fascinating place to check out; located in the same building as Squinny’s, this is basically a warehouse where you can buy everything from stuffies to fried dough to Portuguese biscuits to Atlantic cod to linguica and so much more, including all kinds of produce, cheeses, hot sauces, and olive oils. Near Quintal Brothers is Mayflower Brewing Company, a local favorite for ms including one of the best porters you’ll every try.

And if it’s wine you want, head back into the downtown area to Plymouth Bay Winery for an array of wines, including a regional one that is made with cranberries.

Cupcake Charlies
Marc Hurwitz
Cupcake Charlie's / Marc Hurwitz

Because Plymouth encompasses such a large area, there is no shortage of places in which to do outdoor activities. The sea is an obvious choice here, and there really are too many beaches to name, but since some of them are not the easiest places for parking unless you have a sticker, one of the better options is Nelson Beach, which is a short distance north of the town wharf and does has some parking available.

Nelson Beach isn’t as large as, say, White Horse Beach to the south, but it is a beautiful spot with views of the hills in both directions and it is very family-friendly. From Nelson Beach you can take a pleasant walk north along the North Plymouth Rail Trail (also known as Grace Trail) which will bring you to High Cliff, a spectacular spot with endless coastal views southward toward the Cape.

Heading back to the downtown area are walkways along the ocean, one of which leads away from the sea to Brewster Gardens, the Plimoth Grist Mill, and Town Brook Park, all of which follow the beautiful Town Brook — and the historic grist mill happens to have a dining and drinking spot called Lucioso's Pub in case you’re still hungry or thirsty.

Just above the Town Brook area is Burial Hill, an historic cemetery with jaw-dropping views of the town below and the harbor beyond, and a few blocks north along Allerton Street is the National Monument to the Forefathers, and this monument — which honors the Pilgrims -- is almost jarring in its sheer size.

Some of the interior sections of Plymouth to the west of Route 3 are wild, untamed areas with thick pine barrens, sandy hills, bucolic kettle ponds, and peaceful cranberry bogs, all making for an unforgettable outdoor experience.

The aforementioned Myles Standish State Forest is a good place to get a feel for the rugged landscape once you get away from the coast, with the conservation area having well over 10,000 acres of space and including such pristine bodies of water as College Pond, Barrett Pond, and Curlew Pond. Campers will be happy here, by the way, as will hikers, bikers, canoers, kayakers, and folks who like to fish.

The Pinehills has already been mentioned (the Rye Tavern is located there) and it is a good option for walkers and bikers who may want a slightly less remote option than Myles Standish State Forest; this is basically a residential community within Plymouth that has its own little village center in the woods, and it is a nice spot to take a stroll while perhaps visiting a shop or two including the wonderful Market at Pinehills, an upscale grocery store with all kinds of goodies.

Plymouth is one of those places that you could explore for a long time and never get bored, and even longtime residents of Massachusetts are surprised at just how much there is to do here once they start looking beyond the touristy sites. It may be known for its rich history, but that really is just one aspect of this delightful South Shore town.

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