3 Road Trips to Take This Fall

Something about fall makes the open road feel cinematic. Perhaps it’s the crisp air through a cracked window, or the fact that coffee stops and farmstand shops are just better when the leaves are the color of honey and fire. Whatever it is, this season was made for getting a little lost…in small towns, on winding routes, and along the occasional charming detour.

Here are three road trips worth taking this fall, whether you’re craving cozy stays, culinary gems, or just a reason to cue up that melancholy playlist and drive.

Hudson Valley Harvest Tour

Just two hours north of Manhattan, the Hudson Valley is fall in high definition. Wind through Hudson, Rhinebeck, or Kingston, where every antique shop feels like a treasure hunt and farm-to-table menus (and farmstands) are practically religion. Pull over for a tasting of the famous Applejack and apple cider vinegar at Harvest Spirits Distillery, and grab a warm bag of cider donuts from the neighboring orchard, Golden Harvest Farms. Stock up for holiday dinners with gourmet groceries, baked goods, and exceptional prepared foods at Talbott & Arding. And do not, I repeat, do not sleep on the cup of hot chicken bouillon with fresh ginger and star anise. Sip on it while you shop, it’s pure comfort. For impressing even the toughest of gift-givers, shop Batterby House’s collection of antique cookware and curated home goods from emerging brands. 

To Stay: 

• Inness - equal parts rustic and refined, with a design that melds Scandinavian minimalism with rural Upstate farmlands

• Wildflower Farms - set among the Hudson Valley’s natural beauty, this resort is an escape for all of the senses and the ideal setting to unplug 

• The Maker - a bohemian-chic hotel in downtown Hudson, companion to its flagship home shop in New York City

Gilded Weekend in Newport 

Newport, RI, where opulence meets ocean air and every street feels touched by old-world charm. Start the weekend with a slow drive down Ocean Drive, windows down taking in the crip breeze. Tour the Gilded Age mansions draped in ivy, then warm up with an afternoon spent sipping martinis at The Chanler or browsing the boutiques along Thames Street. As dusk hits, head to White Horse Tavern (the oldest restaurant in the US) and enjoy a delicious white tablecloth dinner in the restaurant’s cozy colonial setting. 

To Stay:

• Brenton Hotel - a seaside haven centrally located to the action of Bowen’s Wharf with sleek design, plush rooms, and a rooftop bar with sweeping coastal views

• The Chanler at Cliff Walk - quintessential Gilded Age excellence and period style interiors that encapsulate Newport’s history and grandeur 

Coastal Crawl of Maine

Portland in the fall feels like a well-worn sweater: cozy, unpretentious, and full of character. The salty air mixes with the scent of roasting coffee, chowder, and freshly baked bread as you wander the cobblestone streets of the Old Port. Start your day with a cardamom bun from Standard Baking Co., then linger over oysters, a lobster roll, and crisp white wine at Eventide Oyster Co. before exploring the galleries and boutiques along Middle Street. By night, reserve a table at Scales for incredible New England classics, but with an innovative twist based on what’s in season. 

To Stay: 

• The Francis - a lovingly restored 19th-century mansion with locally inspired design 

• Longfellow Hotel - luxurious and thoughtfully tailored for the stylish, wellness-lover