Beyond Boston: Visiting Salem, Gloucester, Rockport, The Berkshires, and Plymouth

Take a 4–day trip, or individual 1-day trips, beyond the city of Boston and explore some of the best places in Massachusetts.

Welcome to “Part 2” of the ultimate Boston and Beyond vacation! My husband, 2 teenagers and I spent 8 days in June exploring my home state of Massachusetts. We began our trip with 4 days in Boston. (Check it out: 4 Days in Boston: Food & Fun)

We had a blast in Boston, but I also wanted to take the time to get out of the city and show my family some other highlights of Massachusetts, including seaside towns and the mountains. So we rented a car and made a big circle around the state with stops at Salem, Gloucester, Rockport, The Berkshires, and Plymouth.

We experienced all 5 areas in just 4 days without feeling rushed! However, if you only have one day, Salem, Gloucester, Rockport and Plymouth are all great as individual day trips from Boston. The Berkshires is about a 3-hour drive, so you would want to plan for 1-2 days, perfect for a weekend getaway.

4 Days Beyond Boston: What To Do and Where To Eat

Whether you follow our itinerary for 4 consecutive days or plan individual day trips, you’ll need a car! We rented our car at Logan International Airport. This made it easy to return the car at the airport and catch our flight home.

Salem

Day 5 of our 8-Day Boston & Beyond Vacation

Salem, Massachusetts is a short 35-minute drive north of Boston. When you arrive, park in the parking garage across from the Visitor Center, 2 New Liberty St. The restrooms at the Visitor’s Center are great, plus you can pick up a free map which directs you to follow the Salem Heritage Trail Red Line, which guides visitors to all the sights.

We decided to skip the Salem Witch Museum because of bad reviews. So we started at the Witch House Museum (home of a judge during trials) and then stopped for a quick lunch at Boston Hot Dog Company, 60 Washington St.

We continued on the trail to see the Salem Witch Trials Memorial and Old Burying Point Cemetery. Then, we took a short walk down to the lighthouse at the waterfront before we headed to Essex Street to do some shopping. We decided to pay the small fee to go inside Count Orlok’s Nightmare Gallery, 217 Essex St., which had a really cool display of movie monsters!

Once we were back to our car, on our way out of Salem, we stopped at The House of the Seven Gables, 115 Derby St., but we skipped the tour.

We spent about 5 hours in this quaint historic town and felt satisfied. I bet Salem is lots of fun to visit in October around Halloween!

Gloucester

We drove the 45 minute scenic route from Salem to Gloucester where we stayed at Cape Ann’s Marina Resort for one night. The on-site restaurant, Mile Marker One, was busy with locals on a Saturday night. We enjoyed a nice dinner along with a nice view of the Marina.

Although I enjoyed the lobster roll (full of lots of meat), I found the bun to be overly-buttered for my taste. The side of coleslaw was decent, but I really didn’t touch the overabundant, blah french fries. Stay tuned because the lobster roll that I had in Rockport was a zillion times better!

Day 6 of our 8-Day Boston & Beyond Vacation

I had researched the best breakfast places in Gloucester and Two Sister Coffee Shop, 27 Washington St., was rated at the top. I agree with the reviews… this was one of the best breakfasts I ever had in a restaurant! You can tell everything is made from scratch in a healthy way.

Although Gloucester is a charming fishing community, we had plans to spend the day in Rockport, about 15 minutes north. If you’re planning a day trip you can easily combine Gloucester and Rockport into one.

Rockport

When my parents lived in Massachusetts (they’ve retired to Florida), they used to spend a day in Rockport for their Anniversary. I actually never went to Rockport, so I was excited to see this seaside village that my parents enjoyed so much.

The center of Rockport is called Bearskin Neck and this is where you’ll find lots of quaint shops, art galleries and eateries. There’s definitely an artsy, laid back vibe. Make your way down Bearskin Neck to the rocky area for some awesome pictures.

We stopped for lunch at Roy Moore Lobster Company, 39 Bearskin Neck. All the reviews said that this was the best place for “lobsta“. A pricey splurge, but well worth it if you’re a lobster fan. You can see them bring fresh lobsters in right behind their shop where the seating area is.

This lobster roll was so much better than the one I had in Gloucester. I loved the simplicity… just a roll and tons of fresh lobster meat. No mayo or other mix-ins.

A couple more places to be sure and see before leaving Rockport…

• The Paper House, 52 Pigeon Hill St, $2 admission. Spend about 15 minutes checking out this unique house and furniture which is made mostly out of newspaper.
• Halibut Point State Park, Gott Ave, $10 parking. This serene and scenic area has several walking trails that lead down to the rocky coast. We spent about 1 1/2 hours exploring and chillin’ on the rocks!

After a full day of sightseeing, it was time for us to make the 3 1/2 hour drive to The Berkshires. We stopped for dinner at Moe’s, off the highway somewhere, then grabbed dessert at Dunkin’ Donuts. (We noticed that Dunkin’ Donuts, or now Dunkin’, is a big deal in Massachusetts. The chain originated in Quincy!)

The Berkshires

We checked into our hotel, Hilton Garden Inn Lenox Pittsfield, around 10 p.m. We were very impressed with this hotel. The rooms were spacious, modern, clean and quiet. Highly recommend.

Day 7 of our 8-Day Boston & Beyond Vacation

We woke up refreshed and ready to enjoy a beautiful day in nature! We started off with a delicious, healthy breakfast at Haven Cafe, 8 Franklin St., in downtown Lenox.

After a hearty breakfast, we stopped at CVS to pick up some bug spray (essential when in the woods) and headed to Mass Audubon’s Pleasant Valley Wildlife Sanctuary, 472 West Mountain Road, Lenox. This area provides lots of hiking trails and access to Lenox Mountain.

The only mountain we’ve climbed as a family was Stone Mountain in Georgia. So, I thought it would be a great experience (and workout) for us to climb Lenox Mountain, which is fairly small. My son enjoyed it! My daughter, on the other hand, was not a “happy hiker”!

After our “fun” hike, we took a short 15–minute drive to visit Hilltop Orchards in Richmond. I read that they had the best Apple Cider Donuts. Yeah, not the healthiest after a hike, but we’re on vacation! These donuts were awesome! We grabbed some extras for later on. In season, this would be a fun place to go apple picking.

We relaxed back in our room for a little bit before enjoying one of the best dinners of the week… at the restaurant in our hotel! So convenient and so good. The restaurant was busy with tourists and locals. Jae’s at the Hilton Garden Inn serves Pan Asian dishes that are big enough to definitely share!

Day 8 of our 8-Day Boston & Beyond Vacation

We’re ready to go home, but we have a full day ahead of us because our flight doesn’t leave until 8 p.m. We had an early, quick breakfast in our hotel room of items we picked up the night before at the “fancy, mini-Whole Foods style” grocery store in front of our hotel… Guido’s Fresh Marketplace.

Plymouth

After a 3 1/2 hour drive, we arrived in Plymouth and were ready for lunch. K Katie’s Burger Bar, 38 Main St., was voted Best Burger South Shore and we can see why! Their burgers are large, fresh, juicy, and come with a variety of unique toppings. Table service or take-out available and it’s only a 5-minute walk from Plymouth Rock.

I loved the Hawaiian Burger, but I have to say I was a little jealous of my son’s burger. He ordered The Vermonter which had caramelized apples and onions, bacon, Vermont cheddar, and creamy maple mayo.

Last on our itinerary, a visit to Plimoth Plantation. We had about 4 hours to spend there, which was more than enough time. Unfortunately, it was a rainy day which made for a less than stellar experience. Honestly, we could have skipped this one. Even if the weather had been nice, it just didn’t seem worth the high-price of admission. Since it’s more of a history lesson, there’s really not much of a “fun-factor” for kids.

Ready to drive back to Logan International Airport and head home with lots of souveniers and vacation memories!

Re-cap of Family Approved Restaurants

Salem

• Boston Hot Dog Company

Gloucester

• Mile Marker One at Cape Ann’s Marina Resort
• Two Sisters Coffee Shop (best breakfast)

Rockport

• Roy Moore Lobster Company

Somewhere off the Highway

• Moe’s Southwest Grill
• Dunkin’

The Berkshires

• Haven Cafe (Lenox)
• Hilltop Orchards for apple cider donuts (Richmond)
• Jae’s at the Hilton Garden Inn (Pittsfield)
• Guido’s Fresh Marketplace (Pittsfield)

Plymouth

• K Katie’s Burger Bar

Interested in spending some time in Boston? Take a look at “Part 1” of our 8-Day Boston and Beyond vacation… 4 Days in Boston: Food & Fun!

PIN ME!!