Boston
You already know the classic, indoor cultural stops here, but Boston has plenty of reasons to get outside come summer, and the city scores high marks for walkability.
Getting here: Fly into Logan International Airport (BOS), with dozens of non-stop flights from most airlines leaving major cities. The airport services a lot of American Airline and JetBlue flights. If you’re coming from a city along the I-95 corridor, Amtrak has three stations in the city.
Getting around: Rent a car on your way out of town, as parking can be a headache. Rideshare to your hotel after touching down.
Where you’re staying: The Revolution Hotel is located where Boston’s South End, Back Bay and downtown all mingle, making it a smart, tactical choice. Just be careful when booking to pick a room with a private bathroom — you’ll want a loft or suite if you don’t want to relive the building’s former life as a YMCA and walk down the hall to wash up. The décor here is urban and utilitarian, with a lot of art splashed around the rooms and in the public spaces. The lobby’s coffee shop is a nice upgrade from gross, who-knows-when-this-was-cleaned-last in-room coffee makers, and the front desk can help with the bike loaners for those bold enough to mix it up with Boston traffic. If you’re bringing a car, the hotel’s rate for a day is as reasonable as the cost of the rooms: about $30.
The hotel is a 15-minute walk from the 185-year-old Public Garden — the first public botanical garden in the United States — and the Boston Common, where you’ll find the Freedom Trail. It’s about twice as far to the Museum of Fine Arts, with its collection that includes Rembrandt, da Vinci and Winslow Homer. It’s not as walkable, especially if you have kids, but the Boston Tea Party Ships & Museum is part reenactment with actors, exhibits and the opportunity to toss some tea overboard into the same water the Sons of Liberty did. Inside, you’ll see the only surviving tea chest from that faithful day in 1773.
What you’re doing: Take advantage of some free entertainment that only costs you time and maybe the price of an iced-coffee. Explore the architecture of the South End, which is only a short walk from the hotel. Hop over to Columbus Avenue, Tremont Street or Washington Street, which are ideal for cruising by foot as you walk along shops, restaurants and a healthy dose of some of the best-preserved Victorian-era row houses in the country. Ride to Fenway Park for an hour-long tour that includes an up-close and personal look down at the Green Monster. Even if you’re not a huge baseball fan, you’ve got to hand it to this park, which is the oldest in the majors, opening just after the Titanic sank.
It’s impractical to think you’ll be able to appreciate all of 2.5 miles and 16 sites along the red-bricked Freedom Trail, which you’ll be sharing with other tourists because the real Bostonians haven’t given it much thought since grade school. But you could walk some of it by heading to the Paul Revere House to take a quick photo and maybe a tour. This puts you in the North End, which is Boston’s Little Italy, and that’s a nice way to spend a few hours. Head to Hanover Street and stop in for a mid-morning snack or a coffee at Modern Pastry, then make your way up to Old North Church to add some perspective to Revere’s ride. If you catch a stretch of bad weather, you can cross over the Charles River into Cambridge and visit Harvard’s Museum of Natural History, where you’ll find exhibits about animals from across the globe. Next-door is the Peabody Museum of Archeology & Ethnology, which delves into a range of topics from the canoes Native Americans used to artwork around the Day of the Dead. If it’s science you’re after, MIT’s on-campus museum covers technology, architecture and Boston’s nautical legacy.
Where you’re unwinding: There will be plenty of opportunity for good beer in Boston, but spend an evening in Haley.Henry, picking at bar snacks like oily fish and crudo over a glass of wine. It might feel like you’re in Madrid but with way different accents. This 2024 James Beard semi-finalist for outstanding wine program offers bottles from around the world, specializing in natural wines. You shouldn’t leave Boston without having at least one pint in an old, Irish pub, and J.J. Foley’s Cafe checks both of those boxes. Since the early 1900s, this place has been a constant in the South End and has everything you want: a giant oak bar top, brick walls, tin ceilings, lots of mirrors behind the bottles, Irish flags on the wall and a beer list that feels familiar. If you’re in Cambridge, Brick & Mortar specializes in cocktails set in a space that gets loud and crowded as guests file in around a circular bar, sometimes with a DJ. This place feels built for everyone, from cocktail lovers to university kids holding onto supermarket beers, so chances are you’ll feel right at home.
Where you’re eating: Cover the basics of coffee and bagels around the corner from the hotel at Berkeley Perk Cafe, where you’ll want to grab a seat by the window to people watch. A bit further up Tremont, you’ll find Mike & Patty’s, which is worth the walk if breakfast to you is a sandwich on a house-made English muffin that might also include a hash brown. For lunch, try to grab a seat at the bright, modern and always crowded Row 34 in the Fort Point neighborhood, where they update seafood classics like topping a fried fish sandwich with yuzu chili aioli and baking saltines from scratch for the clam chowder. If you’re in the North End, Galleria Umberto is the spot for inexpensive but good Sicilian pizza and fried rice balls (arancini), both of which are worth the hassle of the cash-only counter. Lenox Sophia is the tiny restaurant that your in-the-know Boston friend would meet you at for dinner. The five-course prix-fixe menu has options for vegetarians and meat eaters — you both will probably get rice and peas — coming out of a small kitchen that knows its way around duck.
When it comes time to head out of Boston, pick up a rental car — Enterprise has a few locations in town — and drive north on I-93 for about 2.5 hours to reach Carroll in New Hampshire’s White Mountains. A longer, more scenic route takes you from Boston through Salem, Beverly and Portsmouth for lunch, then to Bretton Woods, a village within Carroll, along Route 16.
Bretton Woods
Where you’re staying: The Omni Mount Washington Hotel is a National Historic Landmark built in the Spanish Renaissance Revival style that dates back to 1900, back when it had three train stations that hauled guests in from New York, Boston and Portland, Maine. This is classic New England resort living that specializes in snow sports, making it a bit easier to get around in summer. Rooms here are generously sized, matching the scale of the resort that includes two golf courses, four restaurants, an indoor heated pool and a full-service spa. The Mount Washington embraces its Gilded Age luxury roots and is an example of an older grand hotel, worthy of a Wes Anderson film.
What you’re doing: A resort stay means having options on the property to keep you busy, and the best of the Omni’s offerings might be fly fishing. Try to hook rainbow and brook trout on local streams in the shadow of Mount Washington — part of the Presidential Mountain Range — with a guide or solo with rented gear. For a bit more of an adrenaline rush, the resort can arrange a guide to help you climb the West Wall or take the zip line canopy tour that hoists you about 165 feet off the ground on cables up to 1,000 feet long with mountain views.
While the hotel has some hiking routes, for better views, head to Crawford Notch State Park, where you can challenge yourself to the nearly five-mile Mount Jackson Trail with views down into the valley and plenty of people and pets along the way. The five-mile hike to Arethusa Falls and Frankenstein Cliff is another challenging route to the highest falls in New Hampshire. About 30 minutes away, you’ll find Franconia Notch State Park and its Fume, with a two-mile loop, including a lot of stairs. Here, you walk down a corridor of granite, with walls that rise up to 90 feet high as you listen to running water while walking upstream. On a hot day, you can cool off in the cold waters during a guided waterfall rappelling tour in Franconia. Driving to the summit of Mt. Washington is a thing around these parts — maybe you’ve seen the boastful bumper stickers around town. Auto Road, which opened in 1861, still tasks cars to climb 4,000 feet in elevation. Or you could take in the ride from a different perspective on the Mount Washington Cog Railway. The locomotives here, which were powered by steam until 2008 when diesel engines took over, take you to the summit in about three hours as you climb through three climate zones.
Where you’re unwinding: The hotel has a few bars on site, though the one with the best views is the Observatory Bar on the roof of the main restaurant. The town of Bretton Woods doesn’t offer much, so you’ll have to head out to the next one over, about a 30 minutes west. Schilling Beer Co. is a beer garden with European-inspired lagers and ales, including Italian and Czech styles, where you can sip outside within earshot of the Ammonoosuc River. Around the corner, Littleton Freehouse Taproom & Eatery offers a bit more variety in the food beyond Schilling’s focus on pizza, and the family that runs it has been working in town for 40 years. Expect about 16 beers on tap, mostly from New England, and a constant rotation, including the 6.5% maple breakfast stout from 14th Star Brewing out of Vermont.
Where you’re eating: If you feel like skipping the standard hotel breakfast, Munroe’s Family Restaurant is honest country food where the pancakes are the size of hubcaps. Right on Main Street in Littleton, the sandwich menu at Jack & Fins includes a slam dunk pick, a pressed bacon apple panini where the salty, smoky pork meets a fig jam and tart green apples. Don’t miss the display case full of cupcakes, and take one of each to go and walk around town. You can have a modern, tavern-like dinner at the Beal House, where their Federal-era-style carriage house dining room looks the part with exposed wood beams and a copper topped bar. The menu tends to feature heavier, heartier meals like pork Milanese and house-made cavatelli.
When it comes time to head out of Bretton Woods, drive 2.5 hours southwest, mostly on country roads, to Portland, Maine.
Why Fall Is the Perfect Time to Spend a Weekend in Maine
From lobster rolls to fiery foliage, here is your seasonal guide to the statePortland
Where you’re staying: Blind Tiger Carleton Street puts you in the quieter, residential neighborhood of West End, away from the summer throngs by the waterfront. However, the city is compact and easy to cross on foot, so you’re never really far away from anything. From the hotel, you’re within walking distance of Congress Street and its shops and restaurants. Blind Tiger has two hotels in Portland, but the Carleton Street option offers passes for off-site parking. Rooms are stylishly decorated in vintage furniture and artwork that has an eclectic feel, as if it evolved over time. The building is a beautifully restored, Mansard roof Victorian that dates back to 1869 — it could have belonged to your wealthy and stylish, great, great, great, great aunt.
What you’re doing: Portland’s population swells in the summer with folks trying to claim a bit of Vacationland and lobster. If checking out lighthouses and walking the waterfront is part of the plan, get to them early in the day. There are several good guided tours of the old port, but they tend to start in the late morning or early afternoon. Get up early, grab a coffee and upload maps from Portland Downtown to your smartphone. You’ll cover the architectural highlights near the old port, and it starts at the stately U.S. Custom House, which is on Commercial Street, so you can wander up along that checking out the shops, too. Portland has six lighthouses within a 20-minute drive of the city, though these are likely to be congested with tour buses in the afternoon. If you only have time for one, make it the Portland Head Light, the most photographed, about a 17-minute drive south of the city over the Casco Bay Bridge.
Back on the peninsula, you can walk the Eastern Promenade (from the same designer as Central Park) for a view out over the bay. Closer to your hotel, the Western Promenade runs along a long street of well-preserved, grand homes. Summer is peak time to go island hopping by catching a ride on Casco Bay Lines, which has a terminal on the waterfront. If you’re just looking to ride, jump on the Mailboat Run, which carries mail and freight to five of the islands, and cruise around the bay taking in the views. Casco Bay’s Sunrise Run is a similar idea, but it starts at 5:00 a.m. to catch a glimpse of the sun and takes about 2.5 hours. Peaks Island is the most populated year round and a good choice if you want to get out and walk, or rent a bike for a better way to experience the island and views of mainland Portland.
Acadia National Park, at about three hours away, is a bit of a haul to do in a day, but about an hour away you can see the craggy Maine coast in all its glory at the Giant’s Stairs Trail and McIntosh Lot Preserve. It’s a very short trail — less than a mile out and back to your car — but the views of the unique rock formations on the coast, tidal pools and waves crashing is everything you think of when you picture Maine. Even if it’s not a rain-induced necessity, ducking into the Portland Museum of Art makes for an interesting afternoon learning about Indigenous People and several paintings from Winslow Homer and John Singer Sargent. On the other side of I-295, you’ll find Fore River Sanctuary, an 85-acre preserve that includes White Trail, an easy three mile hike to Portland’s only natural waterfall.
Where you’re unwinding: For small bites and cocktails in Old Port, Blyth & Burrows is a bar where you can start upstairs before sunset, then move downstairs to a separate bar if you stay after dinner and want a darker mood. There are brewery tours in Portland, with bus ride included, but if you only have time to visit one, Allagash Brewing Co. is worth the 15-minute ride off the peninsula for some of the best beer in the country. A little closer is Belleflower Brewing, a family-owned spot in the East Bayside neighborhood that has a solid selection of non-alcoholic drinks. The place, along with its beer cans, are covered in work by local artists. Near the hotel, the Downtown Lounge (606 Congress St, Portland, Maine 04101) is a local watering hole that hits all the right marks: leather booths, familiar cans of beer and patrons who have preferences for their spot at the bar.
Where you’re eating: Portland is no stranger to good coffee and morning sweets; the potato flour-infused Holy Donut should be on your checklist at some point while you’re in town. But for convenience, Tandem Coffee and Bakery is a block over for some of the best java inside a refurbished gas station. And the breakfast treats are baked in house, so try and grab a sticky bun before they sell out. For pizza, Slab cuts thick, square, Sicilian-style slices you can take indoors or outside on the picnic tables. Portions here are massive, so plan on sharing and maybe splitting the prosciutto and fig sandwich on house made bread. The top lobster roll in the city seemingly changes with the tides, but luckily it takes effort to find a bad shellfish sandwich in Portland. The current king of the crustacean is Luke’s Lobster, which has a great location on the pier and a spacious dining room overlooking Portland Harbor. You’ll be able to see dozens of boats tied off and bopping and maybe some lobster cages, though the folks who’ve done the catching are long gone by then. The deck is spacious enough to offer great people watching.
More Like This
This article was featured in the InsideHook newsletter. Sign up now.
