If you are living in the northern half of the United States, that means it’s time for fall. And there’s no place better for an outdoorsy fall getaway than New England. Although some leaf-peepers swear by the classic autumnal scenes of Vermont, the Berkshires or New Hampshire, my go-to for festive September and October weekends is Boston.
You need a long car trip to visit most of rural New England, but Boston is a convenient plane or train ride from pretty much anywhere East of the Mississippi. If the weather turns, Boston is chock-full of museums, events and restaurants that range from simple to gourmet. When the sun is out, you can enjoy the outdoors right in the city, because Boston also has some of the oldest and most beautiful parks in the United States. So grab your Red Sox hat and favorite hoodie, buy a CharlieCard for the T ($2.25 per ride), lace up your L.L. Bean boots and set out to explore these gems!
Friday Night - Getting to town and settling down
Boston is great - but navigating the city’s old streets and modern traffic might not ease your way into a relaxing weekend. You’ll likely be much happier taking the train or flying. If you do drive, park your car and rely on the Metropolitan Boston Transit Authority system (affectionately called ‘the T’) for the rest of your trip.
You’ll have plenty of choices for lodgings, but be aware of some seasonal highs and lows, like when university students arrive. The first weekend in September is the busiest time for freshman college students arriving with their parents, according to Curbed Boston. Hotels may also sell out well in advance around this time of the year.
I love the Liberty Hotel. It’s built in a historic prison, but is one of the most luxurious properties in Boston. The hotel boasts great bars and restaurants, but is also walkable to most of downtown Boston’s sights.
If you’d like to book a night, just click here to get in touch.
Saturday Morning - Smartypants and Smoots
Start your day at Harvard Square in the heart of Cambridge, Boston’s famous ivy league sister city. If you’re planning to jog, grab a quick coffee and donut hole from Dunkin’ Donuts, Massachusetts’ homegrown chain. If you’d like a little more time to relax and enjoy a gourmet brunch before you stroll, Crema Coffee offers specialty brews and an in-house bakery.
From Harvard Square, make your way across Harvard Yard and down to the Charles River. Follow the leafy path along river to the MIT campus. It’s a three-mile walk to the Harvard Bridge, which is 364.4 Smoots long from end-to-end. A Smoot is equal to the length of 5’ 7” MIT freshman Oliver Smoot, whose fraternity brothers measured the bridge by laying him down and painting the markings on the sidewalk. The prank earned Smoot eternal fame amongst the storied ranks of MIT pranksters and the markings remain to this day.
From Harvard Bridge, it’s a 1.5 mile walk along the Boston side of the Charles to Boston Commons, the oldest public park in America. The Commons is also the legendary home to Mrs. Mallard and her eight quacking offspring, stars of the children’s book Make Way For Ducklings. The ducks are immortalized with a statue next to the park’s Swan Boat pond.
Saturday Afternoon - A taste of history
By now, you are likely getting hungry for lunch. Luckily, you’re in the heart of Downtown Boston, which offers plenty of options for every taste and budget. To find the highest concentration of restaurants, head to Faneuil Hall, an 18th-century building converted into three levels of restaurants and retail.
Stick close to downtown Boston on Saturday afternoon by walking the Freedom Trail, a 2.5 mile walk that takes you to 16 revolutionary war sites throughout the city, including Paul Revere’s house and the Old North Church.
Saturday Evening - Head to the ballpahk
If it’s September, you’ll still have time to catch the Red Sox playing the regular season at Fenway Park. This October, they’ll be in the playoffs, but ticket prices will go up. Fenway Park is the oldest and smallest stadium in Major League Baseball, equally famous for its many quirks and devoted fanbase. If you can, try to get a seat on “the Green Monster,” the 37’ 2” inch tall wall in left field that’s thwarted many a right-hand batter’s home runs. You can also try for the lone red seat, 502’ from home plate, that marks Ted William’s home run in 1946, the longest ever hit in Fenway Park.
Fenway Park holds the record for most consecutive sellouts, so make sure to get your tickets in advance. Otherwise you might end up behind one of the stadium’s many view-obstructing poles. As throughout Boston, driving and parking are highly unpleasant, so take the T to Kenmore station (not Fenway) instead.
Sunday Morning - A healthy hike
Start your Sunday morning off with a healthy walk, jog or bike ride through Boston’s Emerald Necklace, an interconnected system of parks that runs from the Commons to Jamaica Plain, Southwest of the city.
The best place to start is the Forest Hills T station. It’s a leisurely six miles back to the Commons, but if you get tired you can always just hop back on the train. The route starts at Harvard’s Arnold Arboretum, where you can wander the paths and watch the fall colors appear. From there, head to Jamaica Pond and climb the Pinebank Promontory for a fine view of the park. Afterwards, follow Riverway Island to the Kenmore/Fenway neighborhood. This bustling neighborhood is the perfect place to stop for a drink or snack. If you’d like to take a longer break, visit the Isabella Stewart Gardner Museum or the Boston Museum of Fine Arts. Once you’re ready to press on, head back to the Boston Commons and you’ll be ready to continue your day in downtown.
Sunday Afternoon - Indian Summer swims
The Atlantic Ocean off the coast of Boston remains swimmable well into September, with water temperatures in the 60’s. The best place to take a dip is Revere Beach, the first public beach in the United States. Only a 20-minute ride on the T from downtown Boston, Revere Beach hosts events almost every weekend, including an annual sandcastle competition and sea kayaking clinic. Even if the weather is too cold to swim, visitors enjoy walking along the beach to spot seabirds and collect shells.
Sunday Evening - Just desserts
With all of your walking, you’ll have earned yourself a hearty meal to wrap up the weekend. Head to the North End for authentic Italian food and local beer. The oldest neighborhood in Boston, this area features over 100 establishments within half a square mile.
If the weather is still temperate, enjoy an al fresco dinner on the numerous patios and sidewalk cafe. Offerings range from Giacomo’s classic hearty family-style meals to Carmelina’s open-air modern cuisine.
Take note that many restaurants are cash-only and there is no T service in the North End, so be prepared to walk out or take a taxi home after your meal.
Going Home
Throughout your busy weekend, you’ll have walked over a dozen miles and tasted some of the best Boston has to offer. But there’s still plenty more to see and do. Luckily, Boston is so easy to get to that you’ll be able to come back soon to pahk ya cah in Havahd Yahd!
If you’d like to discuss your next trip to Boston or anywhere else, just shoot me an email.