My Hometown

Massachusetts may not be on the top of your bucket travel list, but life would not be complete without experiencing the anchor of New England.

Massachusetts is home to the city of Boston, home of the Boston Tea Party, The Old North Church, the U.S.S. Constitution, Cheers…..and Samuel Adams.

For literary buffs, you’ll find the homeplace of Louisa May Alcott when she wrote Little Women, Nathaniel Hawthorne’s House of Seven Gables and Thoreau’s Walden Pond. For history buffs you can re-trace the footsteps of the minutemen who fought the British in the American Revolution. Bar fans can re-trace the steps of Norm from Cheers on the Freedom Trail. Sports fans will have year-round options for live events – The Red Sox, the Celtics, the Bruins….and yes, the Patriots. Massachusetts also includes the iconic summer vacation area known as Cape Cod. (I’ve yet to visit so don’t expect to find itineraries for that here.)

Venture further afield, especially in the fall, to find cozy New England bed & breakfasts, apple orchards and ice creameries scattered among the foliage. Plymouth Plantation (located near Plymouth Rock) offers a chance to visit a real revolutionary village to see how candles were made and cast iron was forged. Or, you can just drive further west to visit the Yankee Candle factory and stock up on your favorite fragrance.

As with your hometown, my favorite places and itineraries are probably not found on any typical website for travel to Massachusetts. Lucky you! I hope you’ll combine some of my suggestions and favorites with the ones you DO find on popular travel sites and that your trip to Massachusetts will be as much of an adventure as life was growing up in Middlesex County!


We will start where it all started…where America became independent from Great Britain.

Boston is a pretty small city. Very walkable, but my favorite thing is that it has an easy-to-navigate subway system (compared to New York for sure). Let’s explore!

Getting There

Fly from anywhere into Logan Airport. Keep an eye on that window as you land, because usually you’ll come in over Boston Harbor and it looks like your gonna land on water. Alternatively, if you are linking a trip to Boston with other points in New England, consider flying into Manchester, New Hampshire. You don’t need a car in Boston, and it is very expensive to park, so price out shuttle service from Manchester to Boston and then rent your car when you are ready to hit the road.

While I recommend the subway for just about everything else, I don’t recommend it for to/from the airport. Just get a cab.

Where to Stay

Boston is not cheap. This is a good time to check out Expedia and price shop. The city is compact, so anywhere is really fine because you can grab the subway easily. There are plenty of brand name hotels if you have points to use.

My personal favorite for price, class and location is Harborside Inn. This is a reclaimed old shipping warehouse and the best-kept secret for accommodations in the city. Located literally 1 block off Quincy Market/Faneuil Hall and the Boston Harbor Waterfront, this boutique property is ideal for your weekend stay.

Fenway Park
Fanueil Hall
Click here to visit the Harborside Inn

Things To Do

The Walrus and the Carpenter Oyster Bar – Quincy Market

Quincy Market & Fanueil Hall

Let’s start with the central hub of any Boston weekend. Quincy Market & Fanueil Hall.

Start working up an appetite by doing a little retail therapy on the old cobblestoned promenade. There’s a mix of local flair and souvenir shops, but there’s also a 5-story Sephora. Be sure to look down as you stroll, as there are quite a few boutiques that are actually below street level.

Hungry? Good. Step inside Quincy Market – that’s the huge, long building you’ve been walking around. It’s essentially the best food court in the world. You can get everything from sushi to gelato, but I recommend you focus on the local flavors of lobster, chowder, raw clams (yes, clams) and cold Samuel Adams.

I suggest an appetizer – find the Walrus and the Carpenter oyster bar and order a dozen cherry stones. That’s what we call “raw clams”. In my humble opinion and after a lifetime of thorough research, I’ll take a briny, salty, chewy raw clam over a wimpy oyster any day. Dash of Tabasco, maybe a little horseradish…down the hatch! This is a good place to try some lobster bisque…don’t get the bread bowl despite the temptation. Have one cold Sam Adams. You’ve gotta save room….

….for the Chipyard. Located on the outside of the food court you will hopefully smell this before you see it. Boston Chipyard Cookies are the perfect bite-sized fresh baked snack. You can ship them, or better yet, ship the raw dough home so you have a memory of your trip to Boston waiting for you.

Union Oyster House’s Oyster Bar

If it’s Friday or Saturday, you might come across Haymarket, Boston’s oldest outdoor produce and fish market. They open at 3am. It’s literally on the side of a road that borders Quincy Market. If you happen to be staying where you can cook, this is the best deal in town on the freshest produce and seafood.

Durgin Park

Other Points of Interest -Quincy Market

Take a few minutes off your feet to listen to the short informational presentation in Fanueil Hall – great overview of the beginning of the American Revolution and what the phrase “one if by land, two if by sea” actually means.

Wander the old cobblestone streets on the perimeter of the marketplace and you’ll find some of the oldest restaurants and taverns in America. The Bell in Hand Tavern is a total well-liquor bar that has been in business since 1795. The Union Oyster House (another good option for raw oysters, or round 2!) has been in continuous operation since 1826. You’ll also find a Boston institution that serves a mix of locals and tourists – Durgin Park. This restaurant advertises “established before you were born” out front and while it has changed hands over the years, each owner has maintained the tradition of communal tables, white-aproned, bawdy-tongued waitresses and the traditional New England menu.

The Sail Loft Boston
Sail Loft Lobster Roll

Boston Harbor Waterfront

Time to venture further afield. Have someone point you toward the waterfront. You’ll cross the street from Quincy Market and find yourself in a harbor-front park. Walk to the left along the sidewalk to Water Street, and look for The Sail Loft. Chowdah time. The Sail Loft has two things that no one does better – the fried haddock sandwich and a mug of clam chowder. Not a bad place to get a lobster roll either.

The Sail Loft’s Award Winning Chowder

Full for a while? Time to explore the waterfront. Depending on time of year and weather, you can take a variety of harbor cruises from here including whale watching. The aquarium is an easy choice too. If you don’t want to venture all the way in, you can usually see the adorable sea otters playing in their pond out front. And that’s free.

Ready to get off your feet for a bit? Try Duck Tours. Great way to see the city, learn some history and scope out other places you might like to see. If you’ve never done a Duck Tour, this vehicle is amphibious and takes a little spin in the Harbor during the tour. Perfect for kids. If this is a little too fun for you, there are lots of trolley tours that leave from Quincy Market including some “hop on, hop off” tours that you can get full day passes for that make accessing popular sites like the U.S.S Constitution, Cheers, and the Old North Church easy.

La Famiglia Giorgio, Salem Street
My family’s favorite place to indulge pasta

The North End

So where to eat dinner? There is only one answer in my opinion. Foodies can find many options in this city, but I was too young to know about those as a kid. The North End is an Italian neighborhood walking distance from Quincy Market with literally hundreds of restaurants, cafes, coffee shops….and pastry shops.

Use your GPS or an Uber to get you to Hanover Street. Anywhere is fine, it’s just a few blocks long. Take some time to stroll and menu-shop. Also consider picking out your dessert location while you’re at it. TIP: For historians, the actual Old North Church is located in this neighborhood.

I’ve eaten at literally dozens of places in the North End. You have a 90% chance of getting a great meal. The secret? Look for crowds of locals or places that require reservations. That’s good sign. There is one place that requires you to line up outside, sit crammed in with strangers and pay in cash. So obviously it’s an institution and an experience, not just a dinner. Giacomo’s is that place, check it out. I remember having a butternut squash and lobster ravioli here that was a best-ever.

TIP: The neighborhood has several “feasts” throughout the year. Check the calendar by clicking the photo below. That is a “not to be missed” experience like no other. Food everywhere, everything smells like it was homemade by your Nona because it was. Truly the flavors of Italy and so much fun.

Giacomo’s North End, Hanover Street
A “feast” festival in the North End – click image to link to a calendar of upcoming feasts

They are famous for the canoli. My preference? A slice of Boston Cream Pie (which is actually a cake) and the champagne cookies (those little shortbreads ones with the rainbow colors and sprinkles).

If Mike’s is too crazy for you, Modern Pastry across the street has great stuff and maybe even a table to sit at so you can enjoy your treats with an espresso or cappuccino.

Time for dessert and another Boston institution.

Welcome to Mike’s Pastries. You’ll see it before you get there. It’s the place with the huge mob outside.

There is no real system as to how you reach the counter and order anything. Just push your way in. now you’re in line. The hardest part is seeing the actual selection before it’s your turn to order. It’s a efficient operation and they have a little more patience than the Soup Nazi, but if you plan to order ten boxes shipped to different parts of America (common here) then try to go on “off” hours (not sure when that is but there must be some).

Copley Plaza/Newberry Street

A short subway ride will bring you to Copley Plaza which is a more city-like cluster of shops and sites. This is where you will find the John Hancock Tower, Boston’s tallest building and Copley Plaza mall, a luxury-shoppers paradise. Also use your GPS to guide you to Newberry Street, just a block away, where you will find blocks and blocks of high-end retail from Kate Spade to Brooks Brothers, art galleries and fancy eateries.

Boston skyline showing the John Hancock Tower
The actual Cheers bar
Swan Boats, Boston Public Garden

Boston Public Garden/Cheers

Just around the corner from straight-laced Newberry Street you will find Cheers, the original and actual bar that the popular tv series was based on. It’s the one downstairs from street level…just like on tv. A bigger, fancier bar is above plus a gift shop where you can buy all sorts of Cheers memorabilia. Time for another cold Samuel Adams!

After you have a refreshed yourself, a short walk will take you to the Boston Public Gardens. This is definitely a spring/summer destination where the locals take full advantage of their short months of warm weather. A swan boat ride is a great way to rest the feet for a few.

This large public park area is close to the Charles River and I highly suggest having someone direct you to the Esplanade/Hatch Shell. This is where the annual Boston 4th of July fireworks display takes place. It’s way smaller than you’d think, but on a pretty day it is a great picnic spot. Dip your feet in the Charles while watching the local college crews row by.

Points of Interest Outside Boston-on subway route

Harvard Square

A short subway ride will bring you to Harvard Square, home to Harvard University. Get your Ivy League on and cruise the campus. There are a few blocks of shopping, restaurants and bookstores appropriate to the neighborhood. One of my favorite off-the-beaten spots here is a Mexican/Cajun restaurant (found this long before I moved to New Orleans!) called Border Cafe. Super loud & lively, long wait, crammed bar, fresh margaritas, house-made flour tortillas…everything you want in a Mexican restaurant.

Harvard University, Cambridge
Border Cafe, Harvard Square
View from seats on the Green Monster, Fenway Park

Fenway Park

No trip to Boston would be complete without a trip to Fenway. Get tickets. Even if you have to get them from a scalper outside. Sooooo worth it. One of America’s oldest ballparks with all the charm. Get a Fenway frank, an Italian sausage or a lobster roll (seriously, what could be better than baseball and a lobster roll?) but definitely have 2 cold Samuel Adams here. If you’ve been here before, consider trying to get tickets to sit on the Green Monster, the famous wall known for being the 2nd furthest outfield wall in the game.

Can’t score tickets? Cram into one of the bars outside the stadium. And yes, have a cold Sam Adams.

Further Afield-past the subway: Stow

If you decide to take a drive, or are heading north to New Hampshire or Maine, here’s a little side trip.

Welcome to my hometown of Stow. A tiny little apple-orchard town about 45 minutes west of Boston.

Here is my list of places worth visiting – including one stop in the town of Bolton next door.

This iconic location is where I won the 6th grade lego contest somewhere around 1985.

Honey Pot Hill Orchards

Just a short walk from the home I grew up in is Honey Pot Hill Orchards, still owned and run by the Martin family. Super charming operation where you can pick your own apples from the tree or just pick up a few varieties in the orchard store. You might also want to grab some cider donuts. Having moved to the south long ago, I now appreciate more than then what it means to taste a fresh apple. What you buy in the grocery just isn’t the same. Throw a bag in your suitcase and make the best apple pie you’ve ever had when you get home.

They have a little zoo set up with an adorable goat playground. There is also a hedge maze. In the fall, they have a pumpkin patch too.

The first people to every hire me. It was a smaller operation then. Now it’s a great day trip for the kids.
Erikson’s Ice Cream. Best on the planet.

Erikson’s Ice Cream

Just a short drive from Honey Pot Hill Orchards is the best ice cream ever made. This seasonal ice cream stand has not changed in the 45 years I’ve been alive to know it.

This is real ice cream folks. Not Breyer’s. Not Blue Bell. Not Ben & Jerry’s (yes, they are from New England but their ice cream is gross). This is The Real Deal. Made from scratch on premises.

The chocolate is so unique. I’ve never tasted the match. The coffee is equally unique. But the black raspberry? I’ve only every come across the flavor once or twice anywhere else in the world. And it never compares.

Erikson’s Black Raspberry ice cream

Hebert’s Candy Mansion

Take a 20 minute drive from Honey Pot Hill Orchards to the town of Bolton. You’ll pass other orchards along the way, feel free to stop and browse the charming country stores that anchor them.

Set your GPS for Hebert’s. This is another place from the nostalgia of my childhood. My real-life Wonka factory. Step inside and smell the toffee, the fudge. It’s being made in house. But what’s that you see across the room? A do-it-yourself ice cream sundae bar!

Wachusett Mountain & Wachusett Meadow Wildlife Sanctuary

Got time for one more detour on your way north? Set your GPS for Wachusett Meadow, about 40 minutes further west of Bolton.

This former farmhouse was a stagecoach stop in the late 1700’s and is now a protected trail system through woodlands and wetlands. You can do a short hike here in an hour or so, or take your time and bring a picnic as there are several great viewpoints on the trails.

Wachusett Mountain Ski Area is nearby if you are staying in the area and want to hit the slopes. This is a small mountain, great for beginners to learn.

This concludes the Massachusetts travel page. If you are planning a New England getaway, be sure to visit my pages on New Hampshire and Maine too!

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