North American Road Trip Part 1: Discovering Boston's Whales, Great Seafood & Revolutionary
- By Chrissy Hamlin
- Oct 8, 2013
- 17 min read

My trip to Boston in 2013 was my first real taste of America - I wasn't sure what to expect when we landed but I knew I was going to have some great seafood and learn a lot more about American History. We had also planned to do some whale watching, as well as following the famous Freedom trail. What I hadn't realized was that I was going to be there on Columbus Day, when the city has a huge parade - so It was a chance for me to witness something intrinsically American on my very first visit. Doing this road trip was going to be quite an experience for me, after Boston we would be driving up to Stowe in Vermont in a very cool Convertible Mustang, then crossing the length and breadth of New York State to drive to Buffalo, where we would be crossing the US/Canadian Border, spending some time in Niagara Falls, and then heading up to Missisauga and Toronto in Canada. But first of all we had a week to discover Boston, one of the most historical cities in New England.
It was the Puritans who first founded Boston as their 'shining city on a hill.' In the following century, the Sons of Freedom were born in Boston, in the midst of a War for Independence. A hundred years later, it was Boston's poets and philosophers who were leading a cultural revolution. Today's Boston is one of America's most forward-thinking and barrier-breaking cities and it's ever changing landscape is now home to some of the country's most cutting-edge architecture. It is predominatley a University City brimming with culture and education. Boston is a place where the old blends in seamlessly with the new. When I visited Boston, it was also still recovering from the terrible terrorist attack which occurred during it's annual Marathon. Adversity makes this city grow stronger and that fact was always evident when chatting to any Bostionian we met.

(Please click on headings to view links to all hotel, restaurant and visitor attraction websites)
My base in Boston was The excellent Westin Copley Hotel, which was ideally located in Back Bay, just minutes from Copley Place shopping Mall, with some some great restaurants nearby, and the main financial district a short walk away.
This hotel is not only determined to provide you with a phenomenal stay and great service, but it also offers guests the opportunity to "Make a Green Choice" and be ultra environmentally friendly. The Westin Copley Place has been the recipient of the prestigious 4-Green Key Award, and it is the only hotel in Massachusetts to be recognized as Green Seal™ Certified.




My stay here was fantastic. The large, spacious room had amazing views out over the city & was well situated for sightseeing and eating out. The hotel staff on Valet Parking will hail you a cab if you want to go anywhere ( or Park and deliver your Car for you ) and the hotel has plenty of great facilities to offer guests staying for both business and lesuire.
Watch my video below for a guests-eye view of The Westin, Copley Place!
THINGS TO DO AND SEE WHILST VISITING BOSTON!
Matthew “Matty” Hughes claims two important places in Boston history. At the tender age of 16 he became the youngest licensed captain ever in the port of Boston, and in 1926 he founded New England’s premier cruise company, what is today the nation’s largest private operator of passenger vessels, Boston Harbor Cruises (BHC).
If you are looking for the ultimate whale watching experience that requires less travel time, offers the most comfortable ride available and gives you more time viewing some of the world's most magnificent creatures then book a Boston Harbour Whale watching cruise in partnership with the New England Aquarium. This is Boston's only 3-Hour Whale Watch, where you'll be taken out to sea on a high-speed catamaran. They will get you to and from the whales in half the time, which allows you more time to actually watch the whales.

The cruise will take you to Stellwagen Bank, the East Coast's most famous whale watching destination. Stellwagen's heavy concentration of humpback, finback, and minke whales guarantees an adventure filled with opportunities to view and learn about whales as they frolic in their natural habitat.
Each Boston Whale Watching Cruise is narrated and guided by a naturalist from the noted Whale Center of New England (WCNE). The WCNE has been studying the whales of New England for more than 20 years and its members are recognized worldwide as authorities on whales.
One of the whales you're likely to spot during a Boston Whale Watching Cruise is the humpback. These Northern hemisphere humpbacks reach an average length of 50 feet, and a weight of about 37 tons! Sadly, they're also among the most endangered, and its estimated that only 8 percent of their original population remains.
With the data collected on each cruise, WCNE is able to further the understanding of whales and their world. And, their presence on board ensures that your whale watch will be an exciting and educational trip.
Whale sightings usually occur on every whale watch. If you do not see a whale on your trip, you will receive a free ticket for a future Boston Whale Watching Cruise. We saw plenty on ours, and although they are sometimes hard to capture on video or film (especially if the boat is rolling and rocking) they are a magical and magnificent sight to see in ther natural habitat - especially when they do a "Fluke" and dive with their tails coming up out of the water.
The catamarans feature 3 outside decks for optimum viewing capability. Inside you will find climate controlled cabin space with cushioned seating, tables, state-of-the-art audio-visual, and a galley offering snacks and beverages for purchase.
We went in October, and despite it being a lovely sunny day on shore, it gets very cold when you are out at sea so make sure you wrap up really well and bring some extra layers to slip on, and some warm gloves. It can also get very windy so wearing hats is or baseball caps is not advised. If you tend to suffer from travel sickness make sure you have some remedies with you - when the sea is really rough it can totally spoil your trip if you feel ill. Food and drink is available to buy on board.
Watch my special "Whalewatching in Boston" Video below and get a taste of what I saw!
The Freedom Trail, is a 2.5-mile, red-lined route that leads you to 16 historically significant sites in Boston. Marked largely with brick, it winds between Boston Common to the USS Constitution in Charlestown. Stops along the trail include simple explanatory ground markers, graveyards, notable churches and buildings, and a historic naval frigate. While most of the sites are free or suggest donations, the Old South Meeting House, the Old State House, and the Paul Revere House charge admission. The Freedom Trail is overseen by the City of Boston's Freedom Trail Commission and is supported in part by the Freedom Trail Foundation and Boston National Historical Park.
The Freedom Trail was originally conceived by local journalist William Schofield, who in 1951 suggested building a pedestrian trail to link together important local landmarks. Boston mayor John Hynes decided to put Schofield's idea into action. By 1953, 40,000 people were walking the trail annually.[3]
The National Park Service operates a visitor's center on the first floor of Faneuil Hall, where they offer tours, give out free maps of the Freedom Trail and other historic sites, and sell books about Boston and United States history.
You can decide to walk The Freedom Trail with an official tour guide or on your own, at your own pace. We did it by ourselves over a couple of days and found it very easy to follow and very informative.
Official Freedom Trail sites - Click on place names for more official info.
Boston Common - Boston Common is a central public park in downtown Boston, Massachusetts. It is sometimes erroneously referred to as the "Boston Commons". Dating from 1634, it is the oldest city park in the United States & is where the Freedom Trail begins.
Massachusetts State House - The Massachusetts State House , is the state capitol and house of government of the Commonwealth of Massachusetts, located in the Beacon Hill/Downtown neighborhood of Boston. The building houses the Massachusetts General Court (state legislature) and the offices of the Governor of Massachusetts. You can easily spot it by it's gleaming gold dome.


Park Street Church - Park Street Church is a historic stop on the Freedom Trail. The founding of the church is predated to 1804 when the "Religious Improvement Society" began weekly meetings with lectures and prayer. The church still holds to its Statement of Faith adopted by the church in 1877. After 200 years, the church is still engaged in current social issues.
Granary Burying Ground - Founded in 1660, the Old Granary Burial Ground in Massachusetts is the city of Boston's third-oldest cemetery. Located on Tremont Street, it is the final resting place for many notable Revolutionary War-era patriots, including three signers of the Declaration of Independence – Samuel Adams, John Hancock, and Robert Treat Paine – Paul Revere, and the five victims of the Boston Massacre.


King's Chapel - King's Chapel, designed by Peter Harrison, was constructed on land taken from the burying ground. To insure the presence of the Church of England in America, King James II ordered an Anglican parish to be built in Boston.
King's Chapel Burying Ground - King's Chapel Burying Ground is the oldest burying place in Boston. The burying ground is the final resting place for many colonists, including John Winthrop, the Colony's 12 term governor; Hezekiah Usher, the colony's first printer; and Mary Chilton, the first woman to step off the Mayflower.
Benjamin Franklin statue and former site of Boston Latin School - The first public school in America was established by Puritan settlers in 1635 in the home of Schoolmaster Philemon Pormont and was later moved to School Street. A portrait statue of Benjamin Franklin overlooks the former site of Boston Latin School which Franklin, Samuel Adams, and John Hancock once attended. Franklin's place of birth was just one block away on Milk Street, across from the Old South Meeting House.
Old Corner Bookstore - Many famous books were published here, including The Scarlet Letter, Walden, and the Atlantic Monthly magazine. The Bookstore was built in 1712 as an apothecary shop, office and home of Thomas Crease. The outspoken Anne Hutchinson, who was exiled from the Bay State, owned the store before it was given to Timothy Harrington who turned it into a bookstore.. The Old Corner Bookstore is one of Boston's oldest surviving structures.
Old South Meeting House - Visit Boston's famed, National Historic Landmark where liberty found its allies and the American Revolution gained its voice. Within the walls of Old South Meeting House, meeting by meeting, vote by vote, a revolution began.
Old State House - Also known as Boston's "Towne House", the Old State House dates back to 1713. This Georgian style structure was occupied by the British during the Revolution and was a continuous reminder to the settlers of British dominance and presence in the colony.
Site of the Boston Massacre - In front of the Old State House, a circle of cobblestones commemorates the Boston Massacre. At this site, tensions between the colonists and British soldiers erupted into violence on March 5, 1770. The relief soldiers that came to the aid of the British were met by an angry crowd of colonists who hurled snowballs, rocks, clubs, and insults. The soldiers fired into the crowd and killed five colonists. Samuel Adams and other patriots called the event a "massacre".
Faneuil Hall - Faneuil Hall has served as a marketplace and a meeting hall since 1742. Inspirational speeches by Samuel Adams and other patriots were given at Faneuil Hall. These oratories became the footstool for America's desire to obtain independence from the British. Faneuil Hall was expanded in 1806 by Charles Bulfinch. When Boston became a city the use of Faneuil Hall as a government meeting place came to an end.
Paul Revere House - Built around 1680, this house is the oldest building in downtown Boston. It served as the home of silversmith Paul Revere and his family from 1770 to 1800. Paul Revere is famous for his "midnight ride" to Lexington, Massachusetts informing Samuel Adams and John Hancock that the British were coming to arrest them. In the 19th century, hundreds of Irish, Italian, and Jewish immigrants to the North End lived in the Paul Revere House and in the 20th century, the house was restored and converted to a museum.

Old North Church - Known as "Christ Church in the City of Boston", this Episcopal church was built in 1723 and is Boston's oldest Church building. On the steeple of this church, Robert Newman signaled with lanterns the approach of the British regulars; "One if by land, and two, if by sea".
Copp's Hill Burying Ground - Copp's Hill Burying Ground is Boston's second oldest burying ground. It was first founded in 1659 as Windmill Hill. The area was named after shoemaker William Copp who once owned the land.Thousands of artisans, craftspeople, and merchants are buried on the Hill. Additionally, thousands of African Americans who lived in the "New Guinea" community at the base of Copp's Hill are buried in unmarked graves on the Snowhill Street side.
Bunker Hill Monument - The Bunker Hill Monument stands 221 feet tall at Breed's Hill, the site of the first major battle of the American Revolution fought on June 17, 1775. "Don't fire until you see the whites of their eyes" is the legendary order attributed to Colonel William Prescott to make sure that each shot would count. The poorly trained and ill prepared colonial forces repelled two major assaults by the British Army before retreating. Almost half of the British soldiers were either killed or injured. Although the colonists lost the battle, their bravery and strong showing against the British encouraged them to fight on.
USS Constitution - USS Constitution is the oldest commissioned warship afloat in the world. It was first launched in 1797. Constitution is one of six ships ordered for construction by George Washington to protect America's growing maritime interests. The ships greatest glory came during the war of 1812 when she defeated four British frigates which earned her the nickname "Old Ironsides," because cannon balls glanced off her thick hull. The ship was restored in 1927 with contributions from the nation's school children.
If you really want to understand Boston History, then you must visit this top tourist attraction. It is an entirely new kind of museum, where you’ll not only view artifacts of historical importance, you’ll also have an all-encompassing, multi-sensory experience. At the Boston Tea Party Ship, the museum experience will transport you on an incredible journey back in time as you take part in the famous event that forever changed the course of American History!




Located on the Congress Street Bridge in Boston, Massachusetts, this floating Boston Museum uses Live actors, high-tech, interactive exhibits, authentically restored tea ships and the stirring, multi-sensory documentary “Let it Begin Here,” to bring history alive. Meet the colonists, explore the ships and dump tea overboard just as the Sons of Liberty did on that fateful night of December 16, 1773. Stop in at Abigail’s Tea Room and visit the Gift Shop for special souvenirs. It’s educational, entertaining and enlightening — an experience not to be missed. The tour tour of the Boston Tea Party Ships and Museum lasts approximately one hour and will take you through a variety of virtual exhibits, that are all interconnected. The tour is designed to give you the opportunity to participate, explore and learn about the people, events and consequences that led up to the American Revolution in the order in which they actually occurred more than 230 years ago.
Inspired by a group of Holocaust survivors who found new lives in the Boston area, the New England Holocaust Memorial was built to foster reflection on the impact of bigotry and the outcomes of evil during World War II and to this day. The Memorial represents the effort of more than 3,000 individuals and organizations, coming together to create a vibrant beacon of memory—and hope foster memory of, and reflection on, one of the great tragedies of our time. The New England Holocaust Memorial is an outdoor space, open and accessible to the public at all times. It is located in Carmen Park on Congress Street near Faneuil Hall and Quincy Market, on Boston’s historic Freedom Trail.



If you don't fancy walking the Freedom trail then an alternative to seeing a lot of sights in the city in one go is to do a Boston Duck Tour. The “DUCKS” are W.W.II style amphibious landing vehicles and there are two different routes and tours. First, you’ll be greeted by a ConDUCKtor®, who’ll be narrating your sightseeing tour of Boston. You’ll cruise by all the places that make Boston the birthplace of freedom and a city of firsts, from the golden-domed State House to Bunker Hill and the TD Banknorth Garden, Boston Common and Copley Square to the Big Dig, Government Center to fashionable Newbury Street, Quincy Market,the Prudential Tower, and more. As the best of Boston unfolds before your eyes, your ConDUCKtor® will be giving you lots of little known facts and interesting insights about this unique and wonderful city. And just when you think you’ve seen it all, there’s more. It’s time for “Splashdown” as your ConDUCKtor® splashes your DUCK right into the Charles River for a breathtaking view of the Boston and Cambridge skylines. Hop on either one of the 2 different Boston Duck Tours for a quick fun way to see the city!

Irish Famine Memorial - In 1845, a quickly spreading mold began to destroy potato plants in Ireland, unleashing what we now know as the Great Famine. Many of the poor in Ireland depended on potatoes as their primary food source, and about one-eighth of the population died from hunger or disease over the following years. Those more fortunate fled the country, with over 1.5 million Irish arriving in the United States. Boston was a favored place for the Irish start their new lives. To commemorate the 150th anniversary of the Irish Famine, Boston's Irish community unveiled a $1 million memorial park on June 28,1998. Located in downtown Boston, the park is sited along the city's Freedom Trail, and is visited annually by over three million people.

Watch our video on Boston featuring many of the historic sights, other attractions to visit & some truly amazing Food!
What to taste & where to eat & drink when visiting Boston
In a city synonymous with tradition, Boston chefs have spent recent years rewriting culinary history. The stuffy, wood-paneled formality is gone; the endless renditions of chowdah, lobster, and cod have retired; and the assumption that true foodies better visit New York instead is also—thankfully—a thing of the past. In their place, a crop of young chefs have ascended, opening small, upscale neighborhood spots that use local New England ingredients to delicious effect. Traditional eats can still be found but many diners now gravitate toward innovative food in understated environs. Whether you're looking for casual French, down-home Southern cooking, some of the best sushi in the country, or Vietnamese banh mi sandwiches, Boston restaurants are ready to deliver. Eclectic Japanese spot o ya and iconic French restaurant L'Espalier have garnered widespread attention, while a coterie of star chefs like Barbara Lynch, Lydia Shire, and Ken Oringer have built mini-empires and thrust the city to the forefront of the national dining scene.
The fish and shellfish brought in from nearby shores continue to inform the regional cuisine, along with locally grown fruits and vegetables, handmade cheeses, and humanely raised heritage game and meats. But don't expect it to be all boiled lobsters and home-baked apple pie. Today’s chefs, while showcasing New England’s bounty, might offer you lobster cassoulet with black truffles, bacon-clam pizza from a wood-burning oven, and a tomato herb salad harvested from the restaurant’s rooftop garden. In many ways, though, Boston remains solidly skeptical of trends -; the soft frozen yogurt movement has only recently arrived. And over in the university culture of Cambridge, places like East Coast Grill and Oleana, espoused the locavore and slow-food movements before they ever became culinary buzzwords.
Some of my personal restaurant recomendations are:
Legal Seafoods, - 26 Park Plaza, Boston - This lively Legal Sea Foods’ location in Boston’s Theater District, surrounded by hotels and nearby Newbury Street, Copley Square and Boston Common, offers fantastic seafood and an expanded wine menu. inside you’ll see a two-story cascading fountain, the center-piece of the restaurant which has a dining room and a comfortable lounge three floors below. Their award-winning Wine Cellar, which holds over 10,000 bottles and 800 different labels, is also situated downstairs. Call ahead and ask the wine steward for a personal tour. Try the New England Clam Chowder - possibly the best in Boston.

The Cheesecake Factory - The Shops at Prudential Center,115 Huntington Avenue - This chain restaurant serves Breakfast, Brunch, Lunch and Dinner as well as many varieties of Cheesecake. Try the Eggs Benedict for a real treat for Sunday Brunch. The menu is huge and you can get practically anything including Seafood, Burgers, Steaks. Pasta and Vegetarian options. The Cheesecake Factory menu features more than 200 selections made in-house each day, using only the highest quality ingredients. The Interior is also noteworthy for it's marble pilars and painted ceilings.



The Union Oyster House - The historic Union Oyster House, located on the Freedom Trail, near Faneuil Hall and opposite the Holocaust Memorial, enjoys the unique distinction of being America's oldest restaurant. This Boston fixture, housed in a building dating back to Pre-Revolutionary days, started serving food in 1826 and has continued ever since with the stalls and oyster bar. It was at the Oyster Bar that Daniel Webster, a constant customer, daily drank his tall tumbler of brandy and water with each half-dozen oysters, seldom having less than six plates. In 1796, a future king of France lived on the second floor. Exiled from his country, he earned his living by teaching French to many of Boston's fashionable young ladies. Later Louis Phillippe returned home to serve as King from 1830 to 1848. 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. The Kennedy Clan has patronized the Union Oyster House for years. J.F.K. loved to feast in privacy in the upstairs dining room. His favorite booth "The Kennedy Booth" has since been dedicated in his memory. This is MUST-SEE place to dine when in Boston!





Quincy Market - Quincy Market is a historic market complex near Faneuil Hall . It was constructed in 1824–26 and named in honor of Mayor Josiah Quincy, who organized its construction without any tax or debt. The market was designated a National Historic Landmark, recognizing its significance as one of the largest market complexes built in the United States in the first half of the 19th century. From its beginning, the Market was largely used as a produce and foodstuff shopping center, with various grocers of such goods as eggs, cheese, and bread lining its inside walls. Digging performed for expansion of the market in the late 1970s uncovered evidence of animal bones, suggesting that butchering work was done on-site. The main Quincy Market building continues to be a source of food for Bostonians, though it has changed from grocery to food-stall, fast-food, and restaurants. It is a popular and busy lunchtime spot for downtown workers.



McCormick and Schmicks - McCormick & Schmick's Seafood & Steaks is located at Faneuil Hall Marketplace – adjacent to historic Faneuil Hall. The restaurant is also near many other major tourist attractions such as Boston Common, The New England Aquarium, Old State House and Paul Revere's House. The Menu includes fresh seafood and shellfish, aged steaks and garden fresh salads. The menu reflects seafood from the Pacific Rim, Atlantic Ocean and Gulf of Mexico as well as sourced products from local ranches, farms and wineries to showcase regionally inspired dishes. There is also a beautiful bar area that offers guests a comfortable environment from which to enjoy a wide variety of wines, beers, classic drinks and trendy cocktails. Try the award winning bar food during Happy Hour. Every item on the menu is appealing and the prices are equally attractive!


The Cheers Bar, Beacon Hill - No visit to Boston is complete without having at least one drink in the famous TV bar "Where everybody knows your name" - or more precisley, you can visit the pub that was used as an exterior location for the original comedy show "Cheers". Founded in 1969 as the Bull & Finch Pub, Cheers Beacon Hill became the original inspiration for the setting of the TV show . In fact, the year that the Cheers show premiered on television 1982, Boston Magazine chose the Bull & Finch Pub as the “Best Neighborhood Bar” in Boston. Fans of the show can also visit upstairs where there is a special replica set from the TV Show and a dedicated gift shop for Cheers Memorabilia. There is now another "Cheers" Bar near Faneuill Hall, but the Beacon Hill location was the true original.



The Columbus Day Parade
Boston's Columbus Day Celebrations provide lots of entertainment throughout the 3-day holiday weekend, which always includes the 2nd Monday of October. In 2015, Columbus Day weekend includes Saturday October 10, Sunday October 11, and Monday, October 12. Columbus Day is an official Massachusetts state holiday, which means state offices, banks, and schools are closed, but most other places including stores and shopping malls are open.
Boston's spectacular Columbus Day Parade features an eclectic mix of marching brass bands, military units and Colonial militias, Italian-Boston organizations, Duck Boat floats, politicians, other entertainers, and even vintage autos. It always occurs on the Sunday before Columbus Day. The parade celebrates Boston's Italian heritage, Christopher Columbus's expeditions to the Americas, and the commitment of Massachusetts military units to American freedom. Lots of local organizations, military corps, and high school marching bands provide fun and entertainment. It is also a chance for local politicans and officials to get out on the streets and meet the people - especially if an election for public office is coming up! Many People in the parade throw sweets out to the onlookers as they pass by.
In odd-numbered years (2015, 2017, 2019), the parade kicks off in Boston and winds through the North End's narrow streets - Atlantic Ave, Hanover Street, Cross Street. In even-numbered years (2016, 2018, 2020), the parade marches down Bennington Street in East Boston, starting at the Suffolk Downs parking lot and ending up at Maverick Square.





To find out more about all Columbus Day Festivities for 2015 visit www.boston-discovery-guide.com/boston-columbus-day
Watch our exclusive footage of The 2013 Boston Columbus Day Parade below!