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8 Places You'll Love Visiting on Your Trip to Boston

My husband and I had the fantastic opportunity to travel to Boston last Fall. It is a gorgeous city full of Revolutionary War history, quaint architecture and New England culture. We loved our Boston vacation!

If you're planning a trip to Boston, here are a few places you will definitely want to visit:

1. The Freedom Trail. This is the most popular tourist attraction in Boston. The walking trail begins in Boston Common and takes you past the main American Revolution historical sites.

Boston Common

The Freedom Trail is clearly marked by red bricks or red painted lines running down the sidewalk.

There is a ton of information available about The Freedom Trail, so I'll keep my review brief. It took us about 6 hours to see all of the sights. Most of the sites are free, but some require a few dollars to enter certain buildings. I really liked THIS and THIS site that go into all of the nitty gritty details about the trail. We did NOT get a tour guide and I don't feel like we missed out... we just looked up information on our phone as we went. My only advice would be to wear really really comfortable shoes because you will walk a ton.

Granary Burying Ground, Boston MA

Inside the Old North Church

Paul Revere Statue and the Old North Church

Paul Revere's Home

I do suggest taking time to tour the Massachusetts State House. Free tours are available on weekdays and are hosted by local volunteers. My tour guide had the best Boston accent and knew so many cool things about the history and architecture of the building. It was one of my favorite parts of the trip! For more info on taking a tour of the State House, THIS is the official website.

Massachusetts State House

Inside the Massachusetts State House

I would also suggest timing your walk along the Freedom Trail so that you end up in Little Italy near dinner time. We ate at Giacomo's, where they specialize in Italian seafood dishes. It's always busy and the dining area is super small, so people wait in line outside for a table. It was a memorable experience to be smooshed up next to complete strangers and the food was SO good.

2. Bunker Hill Monument. After touring the main sites on the Freedom Trail, you can continue along the trail walking across the bridge to the Bunker Hill Monument. You have the option of taking the stairs to the top and I recommend it whole-heartedly. My quads were burning and I was sweaty when we reached the top, but the views were unparalleled. So worth it!

Bunker Hill Monument

After visiting Bunker Hill, we walked back through Little Italy and snagged cannolis from Mike's Pastry and Modern Pastry to take back to our hotel. These two pastry shops both claim they have the best cannolis, so we decided to get a couple from each to see who we thought was better. The verdict? We liked them both! Ha!

3. Harvard Yard. (or should I say, "Hah-vahd Yahd") Harvard was founded in 1636 (that just blows my mind!) and is the oldest college in America. It is steeped with culture, history and tradition and is a really neat place to visit. I would recommend taking a free student-led tour to get the most out of your visit because there are so many fascinating stories about the buildings and people who graduated from Harvard. Get info on the tours HERE.

We got really lucky and happened to visit Harvard on a regatta race day. Talk about the ultimate preppy sport. It was SO cool and iconic to see the rowers racing down the Charles River.

We ate dinner at a local student dive called Pinocchio's Pizza. The pizza was amazing and the Italian family that has been running the joint for decades were really friendly and fun. We also heard a lot of good things about Mr. Bartley's Burger Cottage and wanted to eat there, but it was closed the day we visited Harvard.

4. Salem, Mass. Another really cool thing we did on our trip was taking a ferry ride from Boston Harbor along the coast to Salem, Massechussetts. The ferry ride itself was gorgeous. We hugged the coast and saw so many beautiful scenes.

Boston from the Harbor

You can easily get to Salem using public transportation (for a small extra fee) if you don't want to splurge on a ferry ride.

Because we visited in October, Salem was in full-blown Halloween mode. Salem is famous for the Salem Witch Trials and so there's a lot of witch stuff there. At Halloween time, there are street vendors and a carnival-like atmosphere. The voodoo magic shops are strange and the people-watching is even stranger, but we're really glad we went. It was so interesting! Even if you don't have the unique opportunity to visit Salem during the Halloween season, it is still a charming seaside town full of quaint old buildings and was a major shipping port back in the day, so there is a lot of history and charm.

Witch House in Salem

We stopped to get a treat at Ye Olde Pepper Candy Companie, the oldest candy company in America. They specialize in old-fashioned candy and it was a perfect place to get a little mid-day snack. I got a caramel turtle that was divine.

A view of the Custom House from the dock in Salem

For dinner in Salem, we asked a local where he would go to get the best burger in town and he suggested Major Magleashes Pub. It's a total dive bar with awesome burgers at awesome prices. Our burgers did not disappoint! They were thick and juicy and just what we had a hankerin' for. This restaurant is off the beaten path, but just a short walk from the main tourist areas. If dive bars aren't your thing, there are several upscale seafood restaurants along the water's edge that I thought looked fun to try.

5. Plymouth and Cape Cod. One of the days that my husband had to attend some meetings, I rented a car and drove myself to Plymouth and then on to Cape Cod.

When I was researching our trip to Boston, everyone said, "DO NOT DRIVE." So what did I do? I rented a car and drove! I will say that Boston is hands-down the hardest place I've ever driven. Do not even attempt it without a really good GPS system. If you do bring a car, know that parking is expensive. If you are staying in Boston and not venturing to outlying areas, you really don't need a car. Boston is a walking city! The public transportation, nicknamed The T, is really good, safe and cheap. We bought a week-long pass for about $20 and only had to catch a cab once, to the airport, because our flight left at the awful hour of 5am and the subway couldn't get us there in time. Get info about the subway HERE.

If you work up the nerve to rent a car and drive it through the crazy maze that is Boston, know that the white-knuckle driving will only last until you get out of the city limits. Then it's not bad at all. It's a scenic drive from Boston to Plymouth. Being a western girl through and through, I've never seen so many beautiful trees!

Once you safely arrive in Plymouth, you'll definitely want to visit Plymouth Rock, the site where the Mayflower landed. Then the rest of the sites are really up to you. There are a lot of Pilgrim themed museums and things to choose from. I dropped in at the Visitor's Center and the volunteers there were so helpful. I would recommend stopping in for a free map and a chat to help you decide what you want to see.

Plymouth Rock

Jenny's Pond, Plymouth Mass.

Beautiful church in Plymouth, Mass.

After visiting Plymouth, I kept driving to Cape Cod. Since it was October, it was the off-season and most of the touristy stores and attractions were closed, but it was still worth seeing.

Nauset Lighthouse, Cape Cod

Old Higgins Farm Windmill

Even though it was too cold to swim, the beaches were still beautiful and there were so many picturesque sights. I LOVED Cape Cod and want to visit again in the summer so I can go beach hopping and actually swim. I have heard that it can get very congested on the weekends in the summer, so plan accordingly.

Boardwalk in Sandwich, Mass

6. Copley Square. Copley Square is a historic area in Boston that features three main attractions: The Boston Public Library, Trinity Church and Old South Church. I was a little unsure about visiting the public library. After all, we have a public library back home. Well, not like THIS one! It is full of ornate architecture, gorgeous statues and surprises around every corner. Take a few minutes and wander around this amazing building.

Trinity Church is also an architectural wonder and was even named one of the ten most architecturally significant buildings in the United States. The stained glass windows were astounding and for $7 each we were able to take a self-tour of the building, which included a map that explained the stories behind each window. HERE is info on the tour.

Old South Church was a significant place during the Revolutionary War, thanks to the Sons of Liberty, whose meetings there were precursors to the Boston Tea Party. When we visited, someone was practicing the big, powerful organ in the chapel and the music was so beautiful it brought me to tears. There are no guided tours that I know of, but the building is open during normal hours and it is definitely worth stopping in to see (and hopefully catch an impromptu organ concert!)

7. Boston Museum of Fine Art. If you are an art lover, the Boston MFA was top notch.

When I visited, I was able to see paintings by the likes of Monet, Renoir, and Cezanne. There was a huge range of exhibits... everything from mummies to Roman statues to crazy modern stuff. The MFA also features a few recreations of historic rooms decorated according to certain time periods. They were one of my favorite parts of the museum! I spent about 6 hours there and saw pretty much everything. You could spend two or three hours there and just hit the highlights if you can't commit to an entire day. There is a cafeteria and a restaurant in the museum if you get hungry, but they were a little on the pricey side.

8. One last suggestion of something to do in Boston... take a walk through some residential neighborhoods. Even an "average" street in Boston is brimming with architecture, history and culture. One afternoon I decided to go on a little walk through the neighborhood behind our hotel. It was beautiful!

Beacon Hill is a fantastic place to meander through jaw-dropping neighborhoods. It's kind of fun to just walk around with no destination and be surprised by what you can find.

Acorn Street, Boston

Louisburg Square on Beacon Hill

I would whole-heartedly recommend Boston as a travel destination. I loved the rich history, the beautiful New England foliage, the architecture and the food. It was a wonderful place to visit!
Jennifer V.
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  1. Your pictures are stunning! Oh my gosh, Plymouth and Cape Cod are my favorite places on earth. We are going for another trip this fall to MA, NH and VT and I cannot wait!

    1. Thank you Kristi! I can see why you love them so much. Going once just made me itchy to go again! I would NOT say no to a beach house anywhere in Cape Cod. Seriously, it was amazing!

  2. This is a great list! I especially love to window shop on Newbury Street after a stroll through the Public Gardens. A Freedom Trail pub crawl is on my to-do list this summer/fall. Great information that is really useful for us, thanks for sharing it with…

    Kim -

    1. I walked along Newbury Street. What a unique and charming shopping area! Thanks for stopping by, Kimber!


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