You’re starting to notice dusk settling in sooner, an errant leaf has fallen off a tree in the park, and pumpkin spice memes are beginning to get rehashed. Don’t despair! There’s still time to pull off one last adventure without having to book a transatlantic flight and endure throngs of tourists in Greece.

And if you’re lucky enough to not have kids, this is the ideal time to pack in a trip up the Eastern Seaboard. This itinerary meanders around a bit, touching on upstate NY, Western Mass, and the Maine Coastline and really works just as well in the fall as it does the summer. It’s a mix of contemporary art, shopping, eating, and nature. Of course there’s more things to discover between Astoria and Acadia National Park so if you’re craving more of something specific, let me know and I’ll give you some tips…

A lazy summer night at the Accord Speedway

DAY 1

I’m basing all this on the fact that you’re starting in New York City so feel free to adapt accordingly. Also, it should be noted that East Coast roadtrips always involve a lot of traffic because there’s basically a major metropolitan hub every thirty-seven miles. So be prepared.

Your destination for the night is a very quick drive upstate to the sprawling Inness resort in Accord, New York in the heart of the Catskills. With beautiful cabins done up in understated modern country design and endless landscaping by the one and only Miranda Brooks, this place is a sight for sore city eyes. If all you want to do is relax, don’t leave the property. If you’re in for a bit of adventure there’s the following:

The town of Woodstock is about a half hour away, where you can shop the main street, grab a film at Tinker Cinema, tacos at Tinker Taco Lab, a smoothie at Sunfrost, and hike Overlook Mountain (for you Angelenos out there, this hike is the Runyon Canyon of the Catskills).

The town of Kingston is experiencing quite a revival. Incredible furniture designers like Josh Vogel have ateliers there, you can find James Beard Award-winning Jamaican food at Top Taste, or great country-home goods at Clove and Creek.

At night the Accord Speedway is a fun little dirt pit with demolition derbies and more. And if you don’t feel like the hotel’s restaurant fare, you can grab a tasty pizza nearby at Ollie’s or Westwind Orchard (where you can also slurp cider made in-house).

DAY 2

Head across the river (making sure to stock up on produce at Montgomery Place Orchard) and north to Kinderhook, right to Morningbird Cafe for their exceptional breakfast sandwich, any of their amazing Malaysian entrees, and their UNBEATABLE mochi donuts. Get a latte and some home goods next door at OK Pantry and then walk a block further to Jack Shainman’s sprawling gallery in the town’s former elementary school (though beware, I believe it’s only open on Saturdays).

Then jump in your car and drive ten minutes to one of my favorite art parks anywhere, ART OMI in Ghent. Hundreds of acres of endless fields and woods dotted with works of contemporary art, it is a really special place (and ideal to walk off all the calories you packed in at Morningbird).

From here you’ll cross into Massachusetts and make your way to the slightly-overpriced Tourist motel in North Adams (sadly it’s really the only game in town but the rooms are nice and bright and the minibar well-stocked). This will be your basecamp for tomorrow’s adventure at MASS MOCA. The food at their restaurant is solid, the town is glum so stay on property and make sure to not get here too early! (If you’re looking for other towns to peep between Inness and here, stroll through the main streets of Hudson and Chatham).

Soaking up the sun at Tourists motel in North Adams

DAY 3

MASS MOCA is a massive art center housed in a former New England factory compound. It will take you a few hours to make your way through, and while they always have great temporary shows, the real pieces de resistance are their 3-4 James Turrell installations and the dozens of Sol Lewitt walls. The Turrells require advance bookings so make sure to plan your visit accordingly (I like going to those rooms first when the fewest number of visitors are there).

Now it’s time to head to the coast! You have two options at this point. I’ll always lobby to spend a night in Boston and catch a Red Sox game because Fenway is the most magical stadium in the US, but if that’s not your thing, ignore the next post and go straight to Kennebunkport, Maine.

If you do go to Boston, I highly recommend the Newbury Hotel, right on the park (make sure you request a park-facing room!). You can take a lackadaisical ride on the swan boats, visit the bronze sculpture that pays homage to McCloskey’s ducks, and stroll Newbury Street and its shops on your way to the ballgame.

The Tides Beach Club at Goose Rock Beach in Kennebunkport

DAY 4+5(+6 if you want)

Either this is a day at the ballpark and a drive to Kennebunkport or you are waking up in Maine. In both cases you’ll want to book at least a couple nights’ stay at The Tides Beach Club (and make sure to shell out a few extra dollars for the Jonathan-Adler designed Junior Suite, it’s the only room with a decent-sized bathroom and a beautiful, unparalleled view of the ocean). It’s operated by a company that has a monopoly on the dozen or so other hotels in the area but this is the only one that allows you access to the town’s best beach (Goose Rock). If you stay elsewhere and want to go to this beach you need to get a parking permit at the crack of dawn at the nearby General Store.

Staying at The Tides also allows you access to their beach umbrellas/loungechairs/food, but a little secret is that you are also allowed all this if staying at their sister property, Hidden Pond, and since they never check, regardless of where you stay just arrive and demand chairs while explaining you are a guest at HP, works every time.

Stay at least a couple days here in Kennebunkport because there is just SO MUCH TO DO AND TO SEE beyond the ice cold Maine waters. Below are two short lists, one in town, the other beyond town.

In Town

Your first stop has to be Daytrip Society and Daytrip Jr. run by our dear friends Jess Jenkins and Andy West. Think of them as the perfect outfitters for a weekend in Maine. Forgot a thermos? They have the best one from Japan. Need a blanket for a picnic on the beach? They sourced the ultimate version in Norway. Want to read up on birds and spot them? They got your Swiss binoculars and local ornithology dictionary.

For lunch, the best lobster roll in the country (honestly, they won the award for it) can be found at The Clam Shack. When they ask mayo-or-butter make sure to say “BOTH!” For dinner, it’s all about the kitsch and tradition of Nunan’s Lobster Hut (get here eaaaaarrrlllly to avoid a crazy wait).

Snug Harbor Farms is the most enchanting, magical nursery I’ve ever seen.

For a refined scoop of ice cream right in town go to Rococo’s and get the understated but mesmerizing Honey Vanilla. Closer to Goose Rock Beach is the more indulgent Goose Rock Dairy which is a hot spot come dusk.

Palace Diner: the greatest restaurant in the world.

OUT OF TOWN

The greatest meal of your entire life will be at The Palace Diner. I could do an entire post on this place alone it’s so insane, and I could argue that your entire trip could simply be based around driving directly here for one meal and then heading right back to NYC. Housed in an old box car, its fifteen-seat counter fills up FAST in the summer (like be there by 6a or forget it) and slower in the fall. The menu is simple and straightforward but each dish is NAILED. The pancakes will be the best you ever eat, the tuna melt is worthy of a Nobel Prize, the burger is an embarrassment to all others…Their merch is also off-the chain and beware, this place is CASH ONLY!

A lovely evening excursion involves a stroll through the East Point Bird Sanctuary, seaglass hunting along its rocky tide pools, and a dinner of soft-shell lobster at nearby F.O. Goldwaith’s.

While it’s a bit of a shlep, a midnight visit to L.L.Bean HQ in Freeport Maine is worth every minute. The store never closes, in fact there are no locks on the doors, so you can pull up at 3am to try on some Gor-tex, shoot some arrows, and customize their iconic tote bags.

DAY 6 (AND BEYOND)

At this point you can turn your car around or push further North to Acadia National Park in Northern Maine. If you do, book a room and a meal at Aragosta, on the adjacent Deer Isle. From here, it’s an hour and a half drive to the park where you can hike/boat/swim your days away.

But if it’s time for this magical tour to come to an end, head back to NY along the coast, spending a night at the Vanderbilt in Newport and grabbing a clam pizza at Pepe’s in New Haven the following day before hitting the city traffic and your return to reality.

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