top of page

I will show you how, Boston Massachusetts Now!!!! (Part 2) Harborwalk and Fenway

Updated: Jan 24

Table of Contents

As you can tell I love this City. In Boston Massachusetts there is so much to see and do. I could continue on forever (I really could). In this post I will take you on another walk, part of the Harborwalk, then onto Aquarium, The Secret, Fenway, and of course food. (Lobster baby)

Flying over Boston
Flying over Boston

As I mentioned in part 1, Flying into Boston is great. Views from the airplane are great, and the airport itself is easy enough to get around in. The worst part of it is pickup your rental car. It can be confusing to find the rental car place.

Side note, if you are visiting Southern Maine, New Hampshire, Vermont or Rhode Island. Flying into Boston will save you some bucks.

Harborwalk is huge, and you cannot do it one day, Its over 40 miles long. The city has been working on this for years, trying to make a huge circle of the Harbor/City. I will be taking you on 2 sections of it that I know the most about because I have walked parts of them.

They are South Boston and the area close to the freedom trail. Visit different websites about this area before arriving, there is so much to see and learn. One waterfront, and Boston Harborwalk are the best.

Cruise Critic

South Boston Harborwalk.

Warning: Food will not be cheap.

South Boston Harborwalk at night view
South Boston Harborwalk at night view

Start to the left of Seaport Blvd, in a park that takes you through Fan Pier Park, a busy park with places to sit and people watch or look at the water and skyline There are some real nice restaurants here they are expensive but great with a view of the Harbour. There are also shops, and even a residential area. The Harborwalk continues on and follows right beside the Harbour. This is in my opinion the best view of Boston. I have come here during the day and night and it's beautiful either time.

Stop by the Fan Pier Pavilion roof for another great view of the city and waterfront as you continue your walk. As you continue your walk you will end up at Fan Pier Marina, then onto Valor Park. From there you are a 2- or 3-minute walk to The Institute of Contemporary Art.

This is as far as I have done the walk in South Boston, and honestly, I did not do this all at once, just did bits and sections as I was in the area eating at some of my favorite places.

South Boston Harbour, check out....

  • Lookout Rooftop Bar give great views of the city at night, if you want a drink, try the Lemon Icetail. Located on the corner of Seaport Blvd and Sleeper Street.

  • The Barking Crab-right on the water after you cross the bridge on Seaport Blvd If you don't get lobster or crab, which you should, I have had the Lobster Mac and Cheese which was amazing, and I stole a fried scallop from my friend's plate, and it was yummy too.

  • Sorelle Bakery and Cafe- just south of The Institute of Contemporary Art Try the Bacon Egg and cheese Bagel, Southwest Chicken Sandwich, or the Cubano.

  • Honey Grow- on Northern Ave, on the same block as Sorelle Bakery and Cafe, just one block away from the Institute of Contemporary Art. This place is also affordable, and I have tried it.

  • Legals Sea Foods-with several locations throughout Boston including the airport, Side note, one time I had a layover in Boston, so I had to get a lobster roll from Legal Sea Foods. Still great but not as great as the Half Pound Maine Lobster Roll you will get in South Boston. It is very expensive but amazing views of the harbor.

Freedom Trail area of Harborwalk.

This area is so close to the Freedom Trail you could honestly see parts of both, the same day depending on how you walked it.

I started my day, Parking at the North End Garage Pilgrim Parking) and walked to the Prince Street Park and Tennis Courts. Side note, from this point it is easy to get on the trail that takes up to the waterfront. Prince Street Park is huge, and as you continue you will be beside Steriti Memorial Rink, it is a public indoor ice rink, be careful on hours, but they are usually open in the winter during the day (Heads up they have a snack bar so you can find cheap eats).

Continue on Harborwalk to Puopolo Playground, then Langone Park, then Bocce Ball Courts, as you walk away from the Harbour this is where you will see the plaque of the Great Molasses Flood of 1919. I learned about the flood on the American History Tellers Podcast.

The Secret- Treasure Hunt Book
The Secret- Tresure Hunt Book

Next door is the park that continues onto the Athletic field, but there was a "Secret" here.

Check out The Secret, it's a puzzle book written over 30 years ago. Solve riddles involving cities all around the United States. Figure out the location and dig to find the secret.

It was buried here and found while excavating the baseball field of the park. It is neat to see where a treasure was found more than 30 years after it was buried. If interested in The Secret, buy the book and try to solve a puzzle, or watch Expedition Unknown Hosted by Josh Gates, he does a couple episodes on The Secret. There are still several cities where the riddle needs to be figured out.

From here walk down Commercial Street for a bit, if you look across the street you can see Copp's Hill Terrace, which is right beside Copps Hill Burying Ground from the Freedom Trail. As you continue on Commercial Street you will pass the Constitution Wharf Building, and the US Coast Guard area on the bay. Continue on and you will pass the intersection of Hanover Street, then finally take a left on to Battery Wharf Rd that will take you back onto the Harborwalk trail. But first stop for Coffee at the corner of Battery Wharf Rd at Cafe Amalfi where they have great coffees, pastries, and a great breakfast sandwich.

Check out the Battery Wharf Museum at this point of walk. Continuing on around the walkway it will take you around Battery Wharf Hotel, and Boston Fire Department Marine You will see Boroughs Wharf and Union Wharf as you go. Take a right when the trail stops and walk back out to Commercial Street, then you will see where Harborwalk starts again by turning right and heading towards Pilot House Park on Lewis Wharf, it's just a simple green space but still part of the walk.

Harborwalk will continue on to Commercial Street again which turns into Atlantic Avenue, but Harbour walk leads into another green area where there are 3 mid-range prices restaurants.

The Daily Catch, Boston Sail Loft, and Joe's Waterfront. I didn't eat at any of them on my trip, because I was not hungry due to eating at Cafe Amalfi a while back. But these restaurants look great and in the $20-$30 range. The walk then continues to Christopher Columbus Playground. This is mainly for kids but there is the Rose Kennedy Garden and a trellis, which is nice to see. If you jump off the Harborwalk you will find a great place to eat at the other end of the playground, at the corner of Atlantic Avenue and Cross Street. The Food Shack,

Walk back down the edge of the playground, and you will join the Harborwalk again. You will also see on the other side of the walk, a place to reserve a ghost tour, Boston Marriott, M Lounge, Watering Restaurant and Chart House Restaurant. But what I was interested in was the Water boat Duck House. This is a tiny house built on its own little dock for ducks, it is precious.

As you continue you will follow the dock all the way around and see another Legal Sea Foods Restaurant, but more importantly the New England Aquarium. There are over 2000 animals here and even outside as you go in there is a tank, The pic of the seal is a beauty I saw from that outside tank. Thay are open till 5pm during the week and 6pm on weekends. I highly recommend this place, especially during the week when it is not as crowded. Tickets are only $34 for adults and buy them ahead of time and show them on your mobile device to enter.

After you leave the aquarium the Harborwalk continues, you can buy boat tours in this area, even duck boat tours. This is where my walk ended, and I headed back up to the garage where I parked my car, a quicker way than walking the reverse of what I did on Harborwalk. I took an Uber. lol. I needed to save my knees and feet today.


Last item I want to talk about is Fenway, everyone even if they don't love baseball knows Fenway. Built in 1919, this is a site to take in. Tours happen every day at 5pm, but till 3pm on game days. There are a few types of tours you can take so check out the website to see what you think.

Walking around this area is neat, very bar and music oriented, Cask N Flagon, Bleacher Bar, Foundation Room Boston (House of Blues), Lansdowne Pub, Cheeky Monkey Brewing, and Loretta's Last Call. These are all on the same street, Lansdowne Street. I have been to a few of these when I flew into town at Christmas for a concert at the House of Blues a few years back. That area is definitely a good time.


Places to eat near Fenway.

  • Honey Grow. Boylston Street, I mentioned earlier. I have not eaten at this location, but I am sure the Stir fry is just as delicious.

  • Tasty Burger. Burgers and tots, I tried the Gorgonzola burger. This place is cheap but great. Located on Boylston Street.

  • Citizen Public House and Oyster bar. "What's the Craic" Burger, just try it trust me, it's more expensive but worth it. Located on Boylston Street.

  • Bullpen Kitchen and Tap. I have never tried it, but I have heard good things about it.

I would talk about the hotel I stayed at and the history of it near Fenway, but it closed during the Covid Pandemic and never reopened. Hotel Buckminster, look it up on wiki to learn its past.

That concludes part 2 of Boston Massachusetts, but like I have said I can go on and on about this favorite city of mine, so there may be a revisit soon or a new blog soon. I hope you take a few days and explore Boston, if you can by foot that is great. Explore as much as you can and use Uber or taxis for the rest. Boston is a place that must be explored.

Hilton Honors

This page contains affiliate links, which mean if you click and buy, I might make a commission, at no cost to you.


Rated 0 out of 5 stars.
No ratings yet

Add a rating
bottom of page