Boston’s Transformation from Before 1630 into the Future: Downtown Walking Tour

In this walking tour, you’ll hear the stories that connect Boston’s past, present, and future. 

You'll experience popular historic highlights, off-the-beaten-path hidden gems (a few that most locals don't even know about!), and unique traditions that keep this culturally rich and diverse city great. You'll learn why, in our signature "humility," Boston has an official slogan as the "hub of the universe."

You'll cross parts of the Freedom Trail, hearing about the Revolution/War of Independence from the British Empire. You'll also hear of the numerous other "trails" that continue to inspire locals and visitors, such as the Innovation Trail, the Women's Heritage Trail, the Black Heritage Trail, the Irish Heritage Trail, the new Walking City Trails, and even the new Ice Cream Trail!

You'll also hear about some of the challenges we face, such as sea-level rise from climate change and the rising cost of living, as you learn how Boston residents today are working to lead the way toward a livable future for all.

From well before 1630 to today, the people who’ve lived here have many stories worth telling. By sharing where we've been as a city and where we are, we can start to understand where we're headed. As a city that always has an eye on the future, we can imagine this city on its 500th birthday, in 2130.

You'll leave the tour inspired and entertained, with numerous opportunities to pause at some of the city's most iconic and unique photo locations (all photos shown in this listing are my own from the tour route).

*We get on a boat near the end of the tour for a short public transit ferry ride (30 minutes for $7.40 round trip). As you'll hear on the tour, so much of Boston's history has relied on boats and our relationship with the water, and even now, we're in the process of shifting commuters from crowded streets onto the water with more options for enjoyable and efficient water-ferry transit. You'll not only have a scenic and relaxing finish to the tour (both roof deck and covered areas are available), but you'll also be experiencing a part of this hundreds (and thousands) of years-long tradition.*

Start: Atlantic Wharf (Behind the InterContinental Hotel), at the round information booth (see the last photo in the tour slideshow for a map of the meeting area). It's very close to South Station, the main transit terminal of Boston.

Approximate timing:

(1) 45 minutes - Starting at Atlantic Wharf, from the Waterfront Wharf District, along the Rose Fitzgerald Kennedy Greenway, through International Place, and on to the Custom House Tower

(2) 60 minutes - Touring the Financial District, through Post Office Square (including a ~10 minute break partway in a nice cafe for coffee, snacks, and restrooms)

(3) 45 minutes - Tour of the central hub of Downtown Crossing towards Government Center, and on to Long Wharf (occasionally, there will be a festival at City Hall Plaza, which we can stop and appreciate for a few minutes!)

(4) 30 minutes - "I'm on a boat!" from Long Wharf on a Public Transit Ferry for a scenic ride within the Boston Harbor on the Long Wharf/Charlestown "Commuter Rail" route ($7.40 round trip - or take the one way for $3.70 if you'd like to get off in Charlestown Navy Yard to see the USS Constitution / Old Ironsides or the Bunker Hill Monument/Museum)

End: Long Wharf (New England Aquarium)

We'll end in front of the Aquarium Blue Line MBTA station, with a 5-10 minute walk to Haymarket or Government Center for all other train lines and local bus service. There are several other ferries from Long Wharf or Central Wharf as well, depending on seasonal service schedules (toLogan Airport, Hingham/Hull, Seaport/Pier 4, Winthrop, East Boston).

If you are returning to the starting point, it is a 10-minute walk back to Atlantic Wharf, which is 3-5 minutes from South Station (Red Line, Commuter Rail, Amtrak, and Flixbus). 

If you're early:

There are quality public restrooms where signs read "Waterfront Square Gallery." If you have extra time, there is a rotating gallery of art on the ground floor by the restrooms, and an architecture/design exhibit in the BSA Space (Boston Society for Architecture) on the second floor, which is open and free to visit on Monday-Thursday. Parts of the exhibit are visible from the outside, even on weekends. Sorelle is a nice café very close to the starting point, and if you have more time and are looking for lunch beforehand, try the High Street Place Food Hall (closed on Sunday), the rotating selection of Food Trucks by South Station in front of the large mural at Dewey Square, or James Hook & Co. for one of the top places to get a lobster roll (large quantity, two people could share one lobster roll).

FAQ:

• Not sure about whether the full tour might be too long? We’ll take breaks along the way, with opportunities for a snack, coffee, and restrooms, plus you’ll have a nice rest on a water ferry ride near the end.
• In winter, we will take many indoor stops with heating!
• In summer, we will take many indoor stops with air conditioning!
• If you want to get off the ferry in Charlestown, instead of returning to Long Wharf, just let me know!
• If you need to leave early or skip the ferry, just let me know!
• If you are running late, it's often possible to meet us partway if you message me, especially at Liberty Square (~2:30 pm) or at Post Office Square (~3 pm). It is, of course, better if you are there the whole time, so you don't miss any earlier context that helps understand later parts of the tour.
• If you can't find me at the start, send me a message! Boston streets and GPS are notoriously unfriendly with one another, and you might just be on the opposite side of the building, for example. If a tour was cancelled, you'd receive clear messages and suggestions for substitute activities.
• For parking: On Saturdays, your best option is the Post Office Square Garage, with a flat $10 fee all day. On Sundays, all street parking is free if available. Near Post Office Square is a good bet, but if you'd rather not have to think about finding a spot, the Post Office Square garage is the same as on Saturday. On weekdays, it's not recommended to drive if you can help it, as traffic and parking can be horrific (ranked worst in the USA by some metrics!), but if you search on an app like ParkWhiz, you might find a good deal by chance, but if you park further away and take public transit that's best, such as by taking the Commuter Rail into South Station.