Boston, MA: One Day To Do It All

As our trip to the east coast neared, I began to daydream about our arrival in Boston, Mass. It had been nearly 16 years since I toured this ancient US city. I remembered the dingy streets, standstill traffic, old buildings, and massive crowds of people everywhere. This time, I wanted to see more and I wanted to build better memories of this iconic city. My travel partner, Todd Ortega, had never been to Boston. Living only 2 hours away for over 20 years made me responsible for making his experience memorable too.

One of the reasons I hadn’t been to Boston since I was a young woman was its notoriously horrible highway traffic. The city’s main artery, a six-lane elevated highway, ran smack through the historic district and split the city away from the beautiful waterfront. In the words of Pete Sigmund, “like a funnel full of slowly-moving, or stopped, cars (and swearing motorists).” In fact, in the 1980s, the department of transportation predicted traffic jams of 16 hours by 2010. With the two major highways I-93 and I-90 crisscrossing through the city, it would be doomed if something wasn’t done. The vision of two engineers, Bill Reynolds and Frederick P. Salvucci, would forever change the city for the better. But at what cost?

I was so excited about seeing Boston post Big Dig. The Big Dig was the nickname of the city’s major infrastructure changes brought about by Reynolds and Salvucci’s plan. Changes were designed to improve the main arterial roads, transportation systems, and lifestyles of many Bostonians. When the project began in 1982, the estimated budget for the project was a mere $2.8 billion dollars and was supposed to be completed by 1998. “The Big Dig was the most expensive highway project in the U.S. and was plagued by escalating costs, scheduling overruns, leaks, design flaws, charges of poor execution and use of substandard materials, criminal arrests, and even four deaths.” (WP)

In 2007, 25 years later, the Big Dig would finally be considered complete, or at least the majority of it was. The project actually cost $14.6 billion but will accrue interest over the next quarter century, bringing the final balance to more than 22 billion dollars by 2038. My unspoken goal for our day in Boston would be to see if this monstrous change would make the city a better place. In other words, was it worth the burden of such a big project from a tourist’s perspective?

A few weeks before we left on our trip, I spent a few hours researching things to do in good ol’ “bean town”. I mapped out our day and to my surprise I found tons of activities, destination points, and plenty of eating options all within walking distance. We would rely on one amazing hotel to make our special day of sightseeing possible, the Marriott Long Wharf Hotel. The Wharf Hotel was situated on the edge of the bay and in the center of it all. Not only is it a five-star hotel, but its service compares to none I’ve experienced.

We arrived in Boston at around 8am after taking the red-eye from Portland, OR. A very quick taxi ride took us downtown from the airport, which was a huge change from the city’s past traffic reputation. In light of not having a rental car to get around, we needed to find a way of storing our luggage. The Marriott bellhop staff offered to hold our bags for the entire day with only a gratuity in return for their gracious service. I called them ahead of time to make sure this was a possibility.

Our flight overnight was less than restful and both Todd and myself were beyond exhausted. As we landed, I thought about what I would say to the hotel manager to get a few hours of sleep before heading out on the town. I would use the crying cat and the turbulent flight as examples for my lack of sleep. To my surprise, the manager offered us a huge discount on their normal rate ($580 per night) to let us nap and freshen up in the hotel. I don’t think we would have been able to manage the whole day of touring the city without this three-hour relief.

After a few hours, we were fresh again. We dropped off our bags with the bellhops and away we went. Directly across from the hotel was the aquarium and the site where we would book our amphibious vehicle tour known as the Duck Boat.

We had most of the day to explore before the Duck Boat tour would leave, so we headed to our first historic spot in the city, the Union Oyster House — America’s first and longest continuously running restaurant. Union Street was built in 1636 and the restaurant’s doors opened in 1826. Since then, “the Union Oyster House has known only three owners. Carrying on proud traditions in dining and service since 1970 have been Mr. Joseph A. Milano, Jr., and Ms. Mary Ann Milano Picardi.” Check out the original menu here.

Even though this place was packed to the gills, we were seated in less than 15 minutes. The staff was incredible and the food was even better than that. We started our meal with Clams Casino, a baked half-shell clam with Asiago cheese, breadcrumbs, a light sauce, and bacon. I had a cup of clam chowder and helped Todd eat the clams before our entrées arrived.

When my shrimp and scallops with sun-dried tomato cream sauce over rice arrived, I immediately dipped my fresh cornbread into the sauce for a taste, and WOW! The sweet and savory tomato cream sauce was light and robust. It didn’t overpower the flavor of the seafood at all and left me craving more despite my full stomach. I was so happy with my dish that I barely noticed what Todd was eating. Though he seemed to enjoy his Basque-style steamed mussels with garlic and white wine broth, I thought my dish was perfect.

The restaurant’s decor was wonderful. It truly embraced its Boston heritage with signs pointing out where famous patrons like John F. Kennedy liked to sit when he visited. Tons of iconic memorabilia decorate the walls. Also, “The toothpick was first used in the United States at the Union Oyster House. Enterprising Charles Forster of Maine first imported the picks from South America. To promote his new business, he hired Harvard boys to dine at the Union Oyster House and ask for toothpicks.” I bet you didn’t know that.

With our bellies full, we hit the streets to kick off our historic journey along the city’s famed Freedom Trail. The Freedom Trail is a 2.5-mile, brick-lined route that leads you to 16 historically significant sites, many historically connected to the Revolutionary War. Each stop was an authentic treasure in history and the trail is now a part of the National Park System.

The trail includes Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel & Burying Ground, Benjamin Franklin Statue & Boston Latin School, Old Corner Book Store, Old South Meeting House, Old State House, Site of Boston Massacre, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, Bunker Hill Monument, and the USS Constitution.
We didn’t get to them all, but we made it to most.

“As the Freedom Trail enters its second half-century, it proudly celebrates that it has become the signature historic experience in New England — attracting over 3.2 million people annually — and has succeeded in preserving the story of the American Revolution and the ideals of freedom of speech, religion, government, and self-determination for all America.” The Freedom Trail Foundation

My favorite stops on the trail were hard to narrow down; they were all amazing in some way or another. With only one day to see the city, these are the stops I highly recommend and a few key elements of why they stood out in my mind. To cover as much ground as we could, we enlisted the pedallers with the local rickshaw or pedal-cab company, known as the Boston Pedicab ( These green-shirted guys are amazing cyclists who work hard to get you to your destination and will help you conquer the Freedom Trail in record time. They gave us a break when the day was at its hottest and brought us to the Boston Commons from Faneuil Hall.

Faneuil Hall

Some of you may already know my obsession with National Parks. Well, Faneuil Hall is the home of Boston’s National Park Visitor Center. If you collect stamps in your N.P. Passport, this is where you want to be. Not only is the hall run and operated by the park system, they offer free city maps, expert advice, and a museum-like setting where you can soak up the history of this great city.

We arrived at the visitor center just in time for the “town meeting”, a re-enactment of a typical meeting where one of history’s most notable events was passionately discussed. Originally, town meetings held at Faneuil Hall between 1764 and 1774 heard Samuel Adams and others lead cries of protest against the imposition of taxes on the colonies. During our re-enacted meeting, we heard from both sides of the debate on the Revolutionary War.

Visitors participated in the debate by reading character info cards as the audience cast their vocal votes shouting “Huzzah!” to give their approval and “Fie!” to show their disagreements with each speaker’s statements. Mixed into the crowd were period-dressed men and women, giving it a truly authentic feel. Learn more about this site by visiting the National Park’s website here.

Old State House

The architecture and historic relevance of this building are the reasons I have added it as one of the best paces to stop on the Freedom Trail. The connection the Old State House has to the incredible story of the Boston Massacre, the beginning of the Revolutionary War, and its role in the Declaration of Independence in 1776 is worth a few minutes of your time.

“Built in 1713, this historic landmark served as a merchants’ exchange as well as the seat of colonial and state governments. In 1761, James Otis opposed the Writs of Assistance here, inspiring John Adams to state, ‘then and there the child independence was born.’ A cobblestone circle beneath its balcony marks the site of the 1770 Boston Massacre when British soldiers fired into a crowd of Bostonians.”

The vantage point for great photos of this site is the corner of Congress and State Streets. The old building is surrounded by skyscrapers dwarfing this elaborately decorated building. Learn more about this great location by visiting the National Park site.

Boston Commons

As America’s oldest public park, it is safe to say that these 44 acres have seen it all. It was purchased by Puritan colonists from an Anglican minister known as William Blackstone. Blackstone originally tried to live with the Puritians but realized he didn’t like them and they didn’t like him. He gave them the rights to the land for 30 pounds and each homeowner paid him 6 shillings a year.

This shared pasture then became known as the Common Lands. Throughout the years, this land was used for the community’s cow grazing, it was home to the Puritan whipping post, and over 1000 redcoats made camp on the common during the British invasion of Boston in 1775. Bonfires and fireworks were set ablaze here to celebrate the repeal of the Stamp Act and the end of the Revolutionary War.

“Here, during the 20th century, Charles Lindbergh promoted commercial aviation. Anti-Vietnam War and civil rights rallies were held, including one led by Martin Luther King, Jr. In 1979, Pope John Paul II celebrated Mass. Today Boston Common, which is located on the Freedom Trail, hosts several citywide festivals and performances throughout the year. It is still open for all to enjoy.

The Common wasn’t always a place of recreation. It also was a site for puritanical punishments, home to a whipping post, and the confining framework known as the stocks. Pirates, murderers, and witches were hanged from the tree known as The Great Elm, now gone.” The Freedom Trail Foundation

We enjoyed the park’s gazebo and statues, the frog pond, and the shade beneath the trees here. As you walk through the park, you will likely see artists, daydreamers, and musicians. The commons is still a place for the city’s best events and is a must see for visitors like you and me.

State House (the new one), the Park Street Church, and the Granary Burying Grounds

Walking north in the Boston Commons, you can’t help but be impressed by the city’s newer State House. This building invoked more from me than the White House in Washington, D.C. did. The gardens were well-maintained and although it was not open the day we were there, it was beautiful to see. From the State House, take a right down the hill alongside the park, then the first left and you will be at the entrance to the Park Street Church and just a few doors down from Boston’s most famous cemetery, the Granary Burying Grounds. These burying grounds are home to more than 8,000 deceased people and a little more than 2,300 markers celebrating the lives of the inhabitants.

“…The central obelisk … marks the graves of Benjamin Franklin’s parents. Alongside the far wall to the southwest is the elaborately embellished marker of John Hancock’s tomb. Toward the rear Paul Revere is buried; a larger marker placed in the 19th Century stands by a small slate marker that dates from Revere’s burial. Bookend monuments in the two front corners of the burial ground represent patriots James Otis and Samuel Adams. Sam Adams had the Boston Massacre victims interred in his family tomb, and so beside the marker of that tomb is one for the victims: Crispus Attucks, Samuel Gray, Samuel Maverick, James Caldwell, and Patrick Carr. On the right hand wall is a plaque marking the tomb of Robert Treat Paine. He along with Sam Adams and John Hancock brings the number of signers of the Declaration of Independence buried in Granary to three.” The Freedom Trail Foundation

•••• Back to our day in Boston••••

We began to make our way back towards the north end of Boston to prepare for our Duck Boat tour, stopping for photo opportunities at the King’s Chapel and Burying Ground, the site of the first public school in Boston (the oldest public school in the country), the statue of Benjamin Franklin, the Old Corner Book Store and the Old South Meeting House. All this history in just a few blocks can be overwhelming. Well, at least it was for us.

As one of the hottest days of the year peaked, we made our way to Rose F. Kennedy Greenway, or Mother’s Park, to enjoy the cool water of the fountain you could jump and dance in. People of all ages were running through the fountain, some fully dressed while others were prepared with swimsuits and towels. I had to cool off, too, so I tossed off my sneakers and ran through the fountain. Once I was cool and wet, I sat to enjoy watching others take relief here. Todd and I laughed at the funny faces we saw as the chilly water hit their heads.

The Greenway is one of many special park areas that replaced the old raised highways during the Big Dig. To look around here now, you would never have imagined that this area was dark, dingy, and lifelessly full of garbage with tons of traffic pulsing overhead. It was nice to reflect and relax here before getting into the amphibious rolling tank known as the Duck Boat.

The Duck Boat driver was full of witty one-liners and historical factoids. It was nice to get a different perspective of what we’d seen along the Freedom Trail, but the best part of this tour was on the waterways of Boston. Todd was one of the lucky ducks who got to drive the Duck Boat in the Charles River.

We got to see a close view of many iconic sites from the river’s edge including Boston General Hospital, the first Yachting Club in the US, and the new Leonard P. Zakim Bunker Hill Memorial Bridge created as part of the Big Dig. The Zakim bridge is now the world’s largest cable-stayed bridge with a whopping 10 lanes of traffic.

As the Duck Boat tour came to an end, our driver pointed out one last site for us: a Berlin Wall Memorial where the largest single piece of the wall now resides. I don’t know for sure what building it was standing in front of or what its significance to the city of Boston was, but it was unique and worth the mention.

The hour off our feet was just enough to strike up a hunger in our bellies. My original dinner destination had a long wait, so we used Yelp to find an alternate. Thanks to Yelp, we not only found an amazing Italian restaurant, Pellino’s, in the North End’s Italian district, but we were able to track down the location responsible for the plethora of identical “Mike’s Pastry” boxes spotted all day long in every corner of the city. We’ll get back to that in a moment.

On our way to Pellino’s, we strolled along the docks on the waterfront towards the jagged roads of the North End Italian district. As we walked up the narrow cobblestone streets, we stumbled upon Paul Revere’s House. The building Revere once called home is the oldest building left in Boston and “one of the few remaining from an early era in the history of colonial America.” Paul Revere House. Unfortunately, it was after-hours so we weren’t able to go in, but I am sure it’s worth the small fee to tour this historic home.

We had a few minutes to kill, so we wandered along Hanover Street, one of the busiest streets we’d seen yet. We stepped inside the very Italian Catholic Church nearby for a moment before returning to the street. If you like Italian food, this is the place to be. I would have to guess that 8 in every 10 storefronts were based on the Italian way of life, be it markets, restaurants, bakeries, or gift shops. The red, white, and green colors were everywhere. If you closed your eyes, you might even hear the old Italian men gabbing about the tourists passing by, most of it in their native tongue.

After a long day, we earned our dinner at Pellino’s Italian Restauranté and our Yelp selection did not disappoint us at all. One of the things I like most about Yelp is the insider’s tips. One of the reviewers noted that the owner was very present here. When we arrived, we were immediately ushered to a small table in the back. The space between tables could not have been tighter, but it was cozy and we never felt as if we were crowded out by other diners. As a matter of fact, we were treated like celebrities, especially after Todd addressed our waiter, the owner, as Don Francesco Pollino. The graceful staff were quick to serve and to please, and Don Pellino made sure we were pleased at every step of our meal. He talked with us about Italy and seemed to dote on us more than any other table in the place.

We started the meal with sparkling water from Italy, fresh calamari with warm marinara made in-house, and the Antipasto Di Casa. The antipasto included homemade salumi, grilled vegetables, fresh mozzarella, bruschetta, prosciutto, beans, greens, and cheeses. Everything was fresh! I almost never have veal, but local veal was something I had to try. The veal Marsala with shiitake mushrooms, caramelized onion-Marsala wine sauce, garlic mashed potato and spinach was rich and flavorful. It was out-of-this-world!

Todd finished his meal before I had a chance to taste it, so I know he enjoyed the lobster ravioli pillows filled with fresh lobster meat, mascarpone-lobster veloute; shrimp and spinach. As we neared completion of our entrees, Don Pellino swung by the table to suggest our dessert be his fresh-made tiramisu. With a flash, he disappeared and reappeared with the decadent dessert. To top it off, he brought out his private stash, an after dinner drink called Limoncello. As he poured us each a small glass, he noted it came from his favorite town in Italy and it was on the house!

What an amazing day in bean town. After exploring this city all day, I can, without a doubt, say that the changes the Big Dig brought to the city were well worth the cost. Everywhere we looked, we saw parks and gardens where there were once overpasses and unused city space. We packed so much into the day that it felt as if we’d been there for a week. Had we really only been on the east coast for 13 hours? We sure made the most of it.

After dinner, we returned to our starting point, the Marriott Long Wharf Hotel, to pick up our luggage and catch the 9 pm train out of Boston’s South Station on our way to New London, CT. We would return to Boston briefly two more times on this trip, once on our way from Manchester, NH to our home base in New London, and another time as we prepared to fly home to Portland. Stay tuned for more about those trips as we make a surprise visit to Fenway Park and compare Boston’s top pastry shops, Mike’s and Modern, to see who really does it best.

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Freedom Trail Map

One thought on “Boston, MA: One Day To Do It All

  1. Pingback: Map Of Boston Freedom Trail | All About Map - Ceamass.Org

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