Boston is one of early America’s most historically significant cities. It is packed with buildings and culture dating back to the 17th century and one of my favorite places to journey as a tour director, tourist and solo adventurer.
So, no matter what my purpose is for visiting, I always walk a portion of the Freedom Trail. This is an inspiring trail that weaves over 2.5 miles through the heart of Boston, past the oldest bits of the city which includes beautiful parks, a golden dome, and past delicious-smelling restaurants.
Read on to see the gems of the city, see the one of the oldest restaurants in America that I finally ate at and the gem of a coffee shop I stumbled across!
I had a few hours to spare between navigating my guests through the old cow path streets and paperwork so I went for a walk. It was near lunchtime so I decided to make my way from Copley Plaza in Back Bay to the start of the Freedom Trail at America’s oldest park (Boston Common), past the State Capitol building and to one of the oldest restaurants in the America’s for a few classic New England dishes. After lunch, I continued my jaunt and came across the best coffee I’ve tasted in New England.
The Public Gardens
Boston’s Public Gardens is my favorite public park in the United States. I love it for its history, its Swan Boats, its manicured flower beds and its charming duck statues.
Created in 1837 as a part of the expansive Emerald Necklace park series that makes up half of Boston’s acerage, the Public Gardens sit adjacent to the famous Boston Common and where I took 20 minutes, paid $3.00 and rode the Swan Boats.
The Swan Boats are as iconic as the Old State House and a must do if you visit the city during the warm months! The boats have been in operation for over 140 years and are beautiful way to soak up the Gardens.
After the Swan Boat ride, I sauntered past the Make Way For Ducklings statue of Mrs. Mallard and her Ducklings whose tale of making a home in the Public Gardens has forever been memorialized in bronze. Have you been to Moscow? Rumor has it that there is a replica of the storybook statue on display.
Next, I crossed the street and began walking up Beacon Hill and past the nation’s oldest park – Boston Common.
Beacon Hill is a posh neighborhood that adorns the highest hill above what was once mudflats.
The Massachusetts State House sits like a golden crown and is hard to miss as you depart from Boston Common. A slight grade will take you past the pine cone, crested dome, first covered in copper by Paul Revere and later guilded with 23 k gold.
Continue past the richest neighborhood in the city and wind your way to the Omni Parker House where you may be tempted to enter in for a dessert.
I made my way past the Parker House which has an extensive list of claims to fame. And, because I have stayed here multiple times, eaten the Parker Hose Roll, licked the plate of the Boston Cream Pie (invented here), and see the rooms made famous by the Saturday Club, I kept walking. But, if you are new to Boston you simply must go inside the building and walk around a bit. The guilded ceilings and dark wood has a smokey appeal to it and it almost feels as if you are walking with the spirit of Charles Dickens and all the famous inhabitants of this historical place.
Continuing along the Trail, I passed the Old South Meeting House which sits on Milk Street, It is here that the Sons of Liberty met and ultimately decided to act out a revolt against the British Crown’s Tea Tax and dump crates of tea into Boston Harbor.
The next gem on the Freedom Trail? The Old State House, built in 1713, is the one of the oldest buildings in the United States and more infamously known for being the location of the Boston Massacre. Currently a museum with a metal medallion marking the infamous spot.
Serving up local fare since 1826, Ye Olde Union Oyster House is one of the oldest restaurants in America and housed in one of the oldest buildings in Boston.
Locals, tourists and celebrities frequent this seafood spot for the variety of locally sourced oysters, lobsters, clams and scrod. Not only are their dishes delicious but this is also where the use of a toothpick became popularized in America.
I enjoyed the little neck clams (steamed) and scrod with a helping of broccoli and cornbread. What is scrod? My waiter informed me that it is a local, young haddock or cod that is filleted and delicately prepared with butter and light spices. A meaty whitefish that the early elites of New England enjoyed.
Bostonian’s originally drank tea but ever since the Boston Tea Party, tastebud preferences know lean towards coffee. On my afternoon walk I came across a fun coffee window on the backside of the Omni Parker House called Boston Brewin’ Coffee. Much to my happy surprise, they are locally owned, locally sourced and organic! Three things that I love! Plus, they were serving up cold brew which is a perfect caffeine fix on a hot summers day!
Cynthia is a recovering Travel Director turned TV host, creator of Her Drive Podcast, and lover of all things adventure, unicorns, van life, and wellness-focused. She can be found dining wherever octopus is on the menu.