Must See New England Fall Destinations in 36-Hours or Less

Now that it's officially fall, cooler temperatures are settling in across New England. But with that change comes the opportunity to explore some of our area’s greatest assets. Here are three worthwhile 36-hour trips within a modest drive of Boston proper to explore on your next free weekend.


1   Photo by Duncan Lake

1. North Conway, New Hampshire

Take in the breathtaking foliage this fall in North Conway, NH. The mecca of hiking in New England, North Conway is the spot where adventurous souls can tackle one of New Hampshire’s 48 4000-footers. Of course, there are plenty of mellower routes for less-seasoned hikers, like one of the Moat Mountains. If you’re looking to explore the outdoors, keep in mind that safety is paramount. Pick a route within your skill level, and don’t forget to pack REI’s Ten Essentials for Day Hiking. From sun protection to extra water, you don’t want to find yourself on a mountain without those essentials.

If hiking is not your thing, there are plenty of other opportunities to explore. Take a drive up the Mount Washington Auto Road or board the Cannon Mountain Tramway to see some epic vistas of Franconia Notch. Wind down at the end of the day with a beer at Moat Mountain Brewery and crispy, delicious pizza at Flatbread Company. Flatbread’s space is super unique, with a massive open kitchen and wood-fired oven. My favorite pizza is “The P.E.,” a delicious blend of goat cheese, Kalamata olives, and fresh herbs. Also, there is only one way to wrap up your trip to North Conway: With an overflowing bacon, egg and cheese breakfast sandwich and heavenly cold brew from Frontside Coffee Roasters. Just keep in mind that traffic is notoriously challenging in North Conway since there’s only one way in and out, so it doesn’t hurt to get on the road early.


3   Photo Courtesy of Allagash Brewing

2. Portland, Maine

If you like food and beer, look no further than Portland. A fun way to kick off the weekend is to explore the Eastern Promenade. Known as the “Eastern Prom,” it’s a foodie’s paradise with a wide array of food truck offerings, including perennial favorites Mr. Tuna, a mobile sushi bar, and Falafel Mafia. The food trucks are located on top of a hill in a massive public green space that overlooks Portland’s spectacular, unencumbered waterfront.

Once you’ve loaded up on some grub, swing through the Old Port and Commercial Street to check out old-school cobblestone streets and partake in some retail therapy. If you’re feeling culturally inclined, hit up the Portland Museum of Art. Incredibly impressive for its size, the museum is well worth the visit. If your trip to Portland is a family endeavor, the brand-new Children’s Museum & Theatre of Maine is located at Thompson’s Point and is chock-full of interactive exhibits.

Portland has an extensive array of breweries, but my favorite must-visit spots are Oxbow Blending & Bottling, Austin Street Brewery’s location on Fox Street, Bissell Brothers and the original pioneer of Maine beer, Allagash. Factory tours are often underwhelming, but the Allagash tour is 100% worth hopping on. Just keep in mind that these tours are almost always sold out the day of, so be sure to book the free tour in advance. The wild-barrel room—which will make you feel as though you’ve been transported to Belgium—is undoubtedly the highlight, and you can sample a beer flight while inside.

After absorbing an appropriate amount of suds, it’s time to bookend the day with more food. Bao Bao, Central Provisions, Eventide, Honey Paw and Salvage BBQ are all worthy visits, depending on your mood. If you’re looking for some evening debauchery, head back to the Old Port and visit Bubba’s Sulky Lounge to recalibrate with some 80’s dance moves, or opt for an outdoor concert at Thompson’s Point or Sea Dogs game at Hadlock Field.


2   Photo by Duncan Lake

3. Portsmouth, New Hampshire

There is no better bang for your buck for a weekend getaway than the 1-hour drive north to Portsmouth, which was recently named “randomly the coolest place in the world” by Patriots defensive end Chase Winovich. Aside from the city’s obvious historic charm, the town’s walkability is a major draw. You can easily stroll around the whole downtown area, perusing unique boutiques and funky shops. There is no shortage of delicious eats in the immediate neighborhood—like The Wilder, Franklin Oyster House, The Goat or Jumpin’ Jay’s Fish Café—but it’s also worth exploring further. Hop in the car and head two minutes down the road to Portsmouth’s up-and-coming neighborhood, the West End, which features a wide variety of restaurants. There’s Ohana Kitchen, featuring Hawaiian-style poké bowls, and Botanica Restaurant & Gin Bar, an intimate French bistro.

The West End is also home to three breweries that are worth a visit. Liar’s Bench, Great Rhythm and Loaded Question are all within walking distance of each other. Whether you’re drawn to a German-style Kölsch, heady New England-style IPAs or Grisette brewed with squid ink, you’re bound to find something intriguing.

Portsmouth’s nightlife appeals to many demographics, with music venues, restaurants and bars. Whether you like something classy or impressively dive-y, this little city has it all. The historic Portsmouth Music Hall is an incredible concert venue that hosts national acts in a very intimate setting. The Press Room is a recently-renovated Portsmouth watering hole that features local musicians with a chill atmosphere. You can also stop by the Thirsty Moose for some chicken wings and questionable late-night dance moves. Although it’s pretty much a lock that you’ll get a Miller High Life spilled on you, it’s probably worth it.

Before hitting the road home, swing by Colby’s for a savory breakfast that will make you feel as though you’re sitting in your grandmother’s kitchen. Make sure to get there early, as seating is limited and you won’t want to leave. Just around the corner is Prescott Park, a beautiful town park with impressively-curated gardens, sculptures and fountains. You’ll want to come back before you know it.