Wicked Walking Tours in Boston, Massachusetts - 24-Hour Travel Guide
Walk through the Fens in Boston's Emerald Necklace (courtesy Flickr: djprybyl)
Somerville is known for Bathtub Mary yard shrines (courtesy Flickr: tracy the astonishing)
The first American flag was flown on Prospect Hill (courtesy Flickr: Eric Kilby)
Spend the evening at Fenway Park (courtesy of Flickr: Paul Keleher)
Overview - Boston is truly a walking city. It is compact and built upwards rather than outwards, which makes it easy to get around on foot. The public transit system is also extensive and reliable. Walking is truly the best way to experience all that Beantown has to offer. Today, we’ll see some of the less trodden paths – forget the Freedom Trail, let’s get off the beaten track and explore the real Boston!
Breakfast - You’re going to be walking around Somerville this morning, so have breakfast at SoundBites Café in Bell Square. It is a very local joint that serves up delicious breakfasts until 3 pm! Their speciality has got to be the strawberry pancakes, so definitely go for those.
Morning -
Somerville is one part of Boston that is explored by relatively few tourists. There are some real gems to be found around the Somerville neighborhood, which is just beyond Harvard University on the Cambridge side of the river. From Bell Square, where you had breakfast, head south to Powderhouse Square, which has a revolutionary-era gunpowder storage house made of stone. On your way, admire the kitchy yard shrines, or “Bathtub Marys” that Somerville homes are famous for.
From here, make for Highland Avenue and walk east down this long road until you reach Prospect Hill. At the top of the hill, you’ll find the tower where the first American flag was flown in 1776. The tower also offers nice views of Boston. From Prospect Hill, you can easily reach Union Square, where you can admire several artistic park benches before lunch.
Lunch - Neighborhood Restaurant and Bakery is a nice place to take lunch in Union Square. They serve very homestyle food, which you can enjoy outside under their overhead grape arbor. The fresh fruit growing on the arbor and the restaurant’s colourful décor make for a lovely lunch setting.
Afternoon -
A short walk over to Harvard Square will get you onto the T, which you can take to Fenway on the other side of Boston. The Fenway-Kenmore district of the city is known best as the home of Fenway Park, where Boston’s baseball team, the Red Sox, play. But the area has a lot more to offer the avid walker. The area known as the Emerald Necklace is a lengthy system of parklands that runs through the city.
There’s far too much greenery to see in one day, so I suggest you take a circular route starting at the Fenway T stop and heading down and around to Emmanuel College and Brookline Ave. This way, you’ll get the full spectrum of the Muddy River and the Back Bay Fens along your walk.
Dinner - Tonight you’re going to enjoy a Fenway Frank hot dog inside historic Fenway Park as you cheer on the Red Sox to a win! Any Red Sox fan will tell you that Fenway Franks are the tastiest hot dogs in the world, which is absolutely true. Grab a dog from one of the walking vendors that peruse the stands, and wash it down with a cold beer. Just don’t miss any home runs!
After Dark - Stay on at Fenway Park until the Red Sox game ends. By then, it will probably be pretty late and you’ll most likely be tired out from such a long day of walking. However, if you’re still up for it, after the game go across to the Cask ‘N’ Flagon, Fenway Park’s most beloved bar. You’ll be sure to see some local color and rowdy Sox fans – just make sure you’re not wearing a Yankees shirt!
Sleep - Stay at the Hotel Commonwealth, located on Commonwealth Ave in Kenmore Square, within easy walking distance of Fenway Park. It’s a good location and the hotel is deluxe standard, with excellent service and beautifully decorated rooms.