Plymouth, Massachusetts is HUGE. I technically live in Plymouth and I’m still almost a 30-minute drive from downtown. Downtown is where you’ll find the famed Plymouth Rock, the supposed spot where pilgrims first landed on North American soil. But honestly? Don’t just come to Plymouth for cringey pilgrim waxed statues, questionable historical references, and a rock on the ground. Actually, you could skip all that and still have a fabulous time.
Downtown Plymouth: Sweets and sunsets
Speaking of theaters, Moonrise is fairly new to Plymouth but fun on a warm summer night (or even a rainy one). They opened during the pandemic when people began to embrace drive-in movies again, and now they’re a popular space for all sort of people to gather. From blockbusters and Rock Horror to Harry Potter and kid films, you can enjoy them all from the comfort of your car. There’s also a beer garden featuring some local brews.
Voted one of the best bakeries on the South Shore, Keegans is a delight to indulge any morning. We happened to wander in near St. Patrick’s Day to snag some Irish cream morning buns and shamrock cookies. The menu changes often, so keep an eye out for double chocolate croissants, strawberry morning buns, and monkey bread. The coffee is wonderful too.
Lots of people opt for a whale watch, but the harbor cruises offer a more laid-back experience. You can order an adult beverage, have a seat on the top deck and watch the world float by as the sun goes down. PS, if you’re interested in visiting nearby destinations, there’s a ferry that leaves the same dock that goes to the tip of Cape Cod – Provincetown!
Go straight to Peaceful meadows after dinner for homemade, generously-sized ice cream. You can thank me later. They have two locations and they’re open late until 10PM most nights.
You have a few fancy spots right on the harbor to have that quintessential lobster roll. But the tired and true (and understated) choice is the Lobster Hut. Step back in time, order up at the counter, and take your prized, fresh seafood to a booth to nosh down. There’s also a bit of outdoor seating overlooking the water and some non-seafood options on the menu. Everything is delicious and wrapped up in New England nostalgia.
Downtown Plymouth: Bars and bites
Martini’s: Classic drinks and food with a slightly older crowd, but the service is often fantastic.
Honey Baby: Brand new, trendy and modern right on the main drag
New World Tavern: Not only does this spot have a zillion beers on tap, they also have a back event space usually filled with jam bands, community theatre, and comedy nights.
Uva Wine Bar: Get a charge-up card and use it on the wine machines to self-serve your own pour. Try a little of each, although the samples are a bit expensive for small selections.
British Beer Company: Dark, cozy, and full of locals, it’s an old-style pub good for last call.
East Bay Grille: Some locals with argue with me this place is overrated, but it’s been my favorite when I’m in town the last fifteen years. It’s a somewhat upscale choice with full menu of tasty local catches and steaks. Service is consistently good, and the new COVID-friendly outdoor bar and massive patio space is wonderful during happy hour with a light harbor breeze blowing.
Along Plymouth’s borders
Plane Jane’s Place at the Plymouth Airport
There’s a small airport in Plymouth that services mostly private planes and routes to the cape. But there’s a fun café right on the tarmac where you can watch live takeoffs and landings. My toddler loves it. Grab a super hearty sandwich, or go early for a tasty breakfast.
Mayflower Brewing and High Limb
There’s plenty of places to drink in Plymouth, but we like brewery-style libations. Mayflower is tucked inside an industrial park but has a large property. You can try a flight at the bar, or if it’s warm, sit out by the picnic tables. Bring the dogs, the kids, and cross your fingers, because sometimes there’s a tasty food truck or two too.
Over at High Limb, cider lovers will find a nice variety to sample – plus a food menu. Have a flight if you can’t commit to just one cider, and pair it with some local cheeses, short rib poutine, or fried pickles.
It’s a little bit of a hike to get to this gem of a restaurant. But if you visit during the warmer months, you’ll feel like you stepped into a secret garden. Rye Tavern is ideal for a cocktail or a romantic, intimate night out. It’s a farm-to-table dining indulgence that sources lots of local ingredients, from coastal sea salt to fresh honey from nearby hives. The menu is always changing seasonally, but have your drinks and dishes out in the garden area and bar, or inside the 1700s tavern on colder days. Here’s the latest menu.
Into the woods: Plymouth woods
Mirbeau Inn & Spa
Even the locals like to splurge at this upscale hotel and spa for a staycation. In fact, my mother and I spent a lovely overnight getting spa treatments, lunching, and falling into luxurious linens at the end of the night. It’s worth finding this oasis in the woods. Have a meal at Mirbeau, or a peaceful afternoon in their saunas, aqua terrace and relaxation room.
Miles Standish State Forest
There are some great paved paths for cyclists, wheelchair users, and people pushing strollers who also want to get out and appreciate nature. You can also camp inside the park with your tent, RV, and even bring your own horse along if that’s your style.
At College Pond there’s some good swimming during the summer, and you can buy a pass to park through the Massachusetts State Park commission. Or, Fearing Pond is another option with deeper waters and often less crowds.
Since I was a kid, this has been the hotspot for field trips. In the 90s a lot of visiting this reenactment village was trying to trick the period actors into talking about television or the internet. Nowadays, they’ve completely rebranded to offer a more realistic insight into life a few centuries ago.
Recently, they changed the name in respect of the indigenous community that reflects both the given “Plimoth” name to the land as well as it’s original “Patuxet” name from the Wampanoag tribe. While representation of both the actual tribal decedents onsite and the actors at the pilgrim village is still quite unequal, there are talks of expansion of the Wampanoag village and more opportunities for equity and education.
Also, if you’re in town for a while, they have some other great programming at Plimoth Patuxet, including a weekly farmer’s market and movie night at their onsite theatre.
If you’re a Plymouth local like me, welcome! Let me know if there’s anything we missed on the list!