Welcome to Boston

With its revolutionary war era history, sports team pride, walkability, and iconic sites on every corner, it’s hard not to fall in love with Boston. In full disclosure, we lived in Boston’s Chinatown area for two years so I am slightly biased. The Boston Run to Remember is one of my all-time favorite half marathons because it takes you through some of the prettiest parts of the city, and as an added bonus, it’s held on the Sunday of Memorial Day weekend so you can stay a full three days and not have to take any time off from work.

Where to Stay

You can get to Boston by flying into Logan airport or by train to North or South Stations. The race start and finish is at the World Trade Center so the ideal place to stay is the Seaport District, the neighborhood directly north of the starting line which has recently become the site of lots of new development. The South End, North End, and Waterfront districts are all nice and walkable to the start too. That said, Airbnbs will book up early and be expensive that weekend, running at least $250/night.

The starting line is also only ~15 min walking from South Station, the main public transportation hub, so as long as you stay somewhere near a metro stop that connects to South Station, you should be in a good spot. Harvard Square, Central Square, Porter Square, and Davis Square are all on the Red Line and Davis (the farthest out) is about 40 minutes to the starting line. Airbnbs run closer to $180/night in Porter Square, but they still book out early.

About the Race

The 5-miler and the half marathon races both start along the same route through the iconic historic district of Boston, passing the State House, Government Center, Faneuil Hall, the Old State House, and Post Office Square. The half marathon also takes you on Memorial Drive along the Charles River, passed the Massachusetts Institute of Technology and with view of Boston University and Boston’s skyline. You’ll end by running along the Boston Common and Public Garden, catching views of the Back Bay neighborhood famous for its tree-lined streets with residential brownstones. It’s truly an epic course route for seeing the city. (Course map)

The race is in honor of fallen first responders, and the pride people have in first response teams is palpable in the air. The aid stations are staffed with volunteer first responder teams, and members of the police department are positioned along the course to keep runners safe and show their appreciation for the fundraising the race brings in. There is a strong sense of community among the nearly 10,000 runners as well as the race organizers and volunteers.

Finally, it’s an extremely well-organized race, and accordingly it consistently ranks in the top races for the state. I ran the five-miler in 2015 and the half marathon in 2016 and would recommend both.

Take full advantage of the long weekend and arrive Friday evening. Ideally, arrive early enough that you can pick up your bib so you can have at least two full days to explore the city. There is so much to do in Boston, it’s worth it to get as much time as you can.

5:00 - Arrive in Boston. Take a ride share or the Silver Line bus from Logan Airport (A) or from South Station (B) to the expo center so you can pick up your bib and skip the trip tomorrow. The expo is open on Friday from 3-7pm and is located at the Seaport Hotel (C).

6:00 - Head to the Airbnb, check in and drop bags off.

7:00 - Head to dinner at Giacomo's (D) at their south end location on Columbus Ave. Unlike their more well-known North End location, this one takes reservations—you should definitely make one as it is a popular spot.

9:00 - After dinner, walk north and cross over the Massachusetts Avenue bridge (E). On the other side, turn back towards the city for a photo-op of the city skyline at night.

**Day 2. See the Historic Sites on the Freedom Trail**

Saturday

Even if you’ve done the Freedom Trail before, I still think it’s still a worthwhile adventure through the city. The route is about 2.5 miles, and is well-marked with a brick line in the road to follow. My preference is to wander slowly but skip going in to the buildings (this takes ~2.5-3 hours). That said, if anything draws you, by all means feel free to go in.

10:00 - Begin your self-guided tour of the Freedom Trail. Have the list of Freedom Trail sites pulled up on your phone so you can read about each as you come across it. The run tomorrow will be that much more satisfying as you’ll be able to recognize the important buildings as you pass them. (Note: I prefer to start at Bunker Hill and work inwards, so you’ll have to start at the bottom and scroll up.)

The first stop, the Bunker Hill Monument, is admittedly a bit of a workout. If you prefer to keep it very light the day before a race, you may opt to skip this and head to the second stop. If you’re game for it, take the Orange Line to the Community College stop (A) and walk about 15 minutes to the Bunker Hill Monument (B). It’s about 300 steps to the top, and it’s worth doing for the view from the top.

11:00 - From there, follow the trail to other historic points in the northeast of the city including, the USS Constitution (C), Copp’s Hill Burying Ground (D), Old North Church (E), and the Paul Revere House (F). As you make your way through the sites, be sure to enjoy North End neighborhood and don’t be afraid to meander through some of the side streets. Eventually you’ll come to Fanueil Hall (G). You should definitely walk around the building and appreciate the history. You’ll probably want to walk through Quincy Market inside, but I don’t recommend stopping for food here as it’s become overrun with chain stores and is usually extremely crowded.

12:00 - Instead of eating at Fanueil Hall, veer off the Freedom Trail briefly and go around the corner to the Boston Public Market (H). This is a relatively new market that houses dozens of local vendors serving food and drinks and selling wares. Enjoy some snacks as you wander.

12:30 - Leaving the Boston Public Market (A), head south for the remainder of the Freedom Trail sites, all of which are within a few square blocks. You’ll first walk through the New England Holocaust Memorial (near A). Then you’ll pass the Old State House (also the site of the Boston Massacre) (B), Old South Meeting House and nearby Corner Bookstore (C), statue of Ben Franklin and Boston Latin school site (D), King’s Chapel and Burying Ground and Granary Burying Ground across the street (E), Park Street Church (F), and the Massachusetts State House (G). Finally, you’ll end the trail by walking through the Boston Common and Boston Public Garden (H).

12:15 - By now you’ve probably worked up a bit of an appetite. Starting where you left off in the Boston Public Garden (A), make your way to Flour Bakery & Cafe (B) on Clarendon Street. They have fantastic sandwiches, salads, and bowls. It is a very popular lunch spot, so it will probably be busy, but they run a tight ship and process orders quickly.

1:00 - Pop back up to St. James Ave. and take in the iconic Trinity Church and John Hancock Tower (C). You can go inside the Trinity Church if you want ($7, open Sat 10am-4pm, Sun 7:45am-8pm, Wed-Fri 10am-4:30pm, closed Mon and Tue) though I don’t think it’s critical that you do. The Hancock building is just neat to see up close.

1:30 - Continue down St. James Ave and it turns into Huntington Ave. On Huntington Ave, you will pass the Boston Public Library (D) (open Mon-Sat 9am-5pm, Sun 1-5pm). Poke your head inside as it is free to enter and has a beautiful interior. Next you’ll come across Copley Place (E), the town square. As you walk down the road further, you’ll pass the Prudential Center (F) on your right. If it is a hot day (not uncommon in late May) or if you need to pick up anything, you can pop into the mall here. Otherwise, continue further until you pass the Christian Science Plaza (G) with its pretty reflecting pool.

2:00 - Take a right on Westland Ave. and you’ll come to the James P. Kelleher Rose Garden (H). Walk on the pathway along the left hand side of the pond heading south.

2:30 - At the bottom of the pond, you’ll find the Isabella Stewart Gardner Museum (I) ($15, open daily 11am-5pm except closed Tues). Perhaps most famous for the art theft that occurred there in 1990, it is my favorite museum in Boston. The Museum of Fine Arts is just across the street if you’d rather do that, but I think the Isabella Stewart Gardner Museum is more worth your time. The museum is the former home of Ms. Isabella Stewart Gardner, an art collector who mandated her home be turned into a museum and kept exactly how she had it during her life. There is a wonderful courtyard in the center of the house. You can see the whole thing in 90 minutes, and you can buy tickets online before you go.

4:30 - On your way back to your Airbnb, complete the loop by walking back on tree-lined Commonwealth Avenue (J).

5:00 - Stop at a grocery store for your pre-race meal shopping. The Star Market that you passed (E) is a good option if you are staying somewhere central. Cook, eat, and head to bed early.

**Day 3.** Race and Recover with Local Brews and Real Italian Food

Sunday

Race day! The race route captures the essence of Boston’s history as well beautiful views from the Charles River. After the race, you’ll recover with a couple of our favorite stops for local Harpoon beer and authentic Italian food in the Little Italy neighborhood of Boston.

5:30 - Wake up and eat breakfast (for us, instant oatmeal and a cup of coffee).

6:15 - Walk to the starting line on Seaport Boulevard near the World Trade Center (A). This is a big race (10,000+ people) so give yourself plenty of time to get settled at the start. Also, the mornings are cool so bring a throw-away layer or trash bag to stay warm.

7:00 - Race! Enjoy the historic tour of Boston on foot and the views from the Charles River Esplanade.

9:30 - Celebrate your finish with a post-race snack. Head back to the Airbnb to get cleaned up.

12:00 - For Brunch, hit up City Tap House (B) (open Mon-Fri 11:30am-12am, Sat-Sun 11am-12am), which has a lot of outdoor seating (which tends to get loud during the after-work hours) and a great beer selection. You can make reservations online for inside.

1:30 - After lunch, head south to Harpoon Brewery (C) (open Sun-Thu 11am-8pm, Fri-Sat 11am-11pm). The brewery tour is totally worth doing. The guides are hysterical, it only costs $5, and you get a ton of samples. Tours run every 30 mins on the weekend and tickets can only be purchased in person (you’ll probably have to stand in line). If you have to wait before a tour (or want to hang around after), then head to the beer hall and have a sampler flight and a homemade pretzel. All of the beer here is great. I’d bring a deck of cards and while away a few hours at one of the outdoor tables.

4:00 - Walk up Seaport Ave to and around the open space near District Hall (there is often some outdoor festival happening in this area.) Pop out to the water around the Institute of Contemporary Art and then continue to walk along the water through the Fan Pier Park. Cross over the Seaport Blvd Bridge, and then head right up the Rose Kennedy Greenway (F).

4:30 - Make your way to Hanover Street and head to Carmelina's (G) (open daily 12-10pm). Yes, I know you’ve already had pasta for the last two nights but seriously, you’re in the North End of Boston, you need to have Italian food tonight. It’s early for dinner so it’ll probably be quiet, meaning you can grab a table near the window. Just to be safe, I’d still make reservations online in advance.

6:00 - If you’ve researched Boston at all, you probably know that cannoli are the thing to get in the North End. Mike’s Pastry and Modern Pastry are both right here if you want one (H). I find them chaotic and stressful but everyone else seems to love them. Bring cash.

7:00 - If the Red Sox are playing at home, you should spring for the tickets and see Fenway Park in all its glory (you can usually find tickets on StubHub for $30-40). (To get there from the North End, take the Green Line from Haymarket to Kenmore, ~30 mins.) Otherwise, another fun option is the Improv Asylum (I), a comedic improv group with shows nightly ($17-25). Enjoy a night out and then collapse with exhaustion.

If you need to leave early on Monday, that’s totally fine—by now I think you’ve seen the best parts of Boston. If you have the morning free and don’t mind carrying your luggage with you (or more ideally, can leave your bags at the Airbnb while they start to clean up), I recommend heading north and visiting Cambridge, the home of two famous universities.

10:00 - Check out of the Airbnb and head to brunch. Walk over the Massachusetts Avenue Bridge (A) to Cafe Luna (B), a brunch place with fantastic food which takes online reservations (score!)

12:00 - After brunch, explore the campus of the Massachusetts Institute of Technology (C) including the famous Barker Library (open Mon-Fri 9am-6pm, Sat-Sun 1-6pm).

12:30 - Continue walking up Massachusetts Avenue. Pass through Central Square (D) and then arrive at Harvard Square (F). It’s about 30 min walking between the two campuses. Stop in at the Harvard Book Store (E) (open Mon-Sat 9am-11pm, Sun 10am-10pm) and wander Harvard’s campus.

1:00 - From Harvard Square, you can take the Red Line to South Station (which also connects to the Silver Line to Logan Airport).