Many New Englanders think of the bridge-adjoined towns of Kennebunk and Kennebunkport, Maine, as summer destinations for well-heeled preppies in pursuit of upcharged clambakes and pristine—if crowded—beaches. However, the savvy weekend jaunter would do well to trade the Nantucket Reds and boat shoes for a scarf and boots: The Kennebunks, most famously home to the Bush family’s summer compound, also make for a cozy offseason retreat for the leaf-peeping set.

And the peeping is good. Come late fall, the Maine coastline is set ablaze in deep reds and burnished golds, providing striking contrast to the craggy jetties and still harbors where sailboats and weathered fishing trawlers remain moored, more for scenery than use as the mercury dips. Moor yourself at the quietly elegant White Barn Inn, nestled in the woods just a short walk from Kennebunkport’s main drag.

The five-diamond resort houses a much-lauded five-star restaurant, and recent renovations that refurbished 11 of the 26 rooms also added a more casual bistro. A steaming mug of whiskey-spiked cider in the lobby provides warm welcome—and the fortitude needed to leave behind the resort’s cushy amenities for a bracing stroll into town (or a bike ride, as the inn offers free rentals, complete with wicker baskets).

Your first stop: Coffee Roasters of the Kennebunks. A large cast-iron roaster serves as the bustling shop’s centerpiece, and a cup of strong, aromatic coffee will run you one dollar—you may think you heard the friendly proprietor incorrectly. After you’ve recovered from this reverse sticker shock, browse the shop’s wares, which include artisanal olive oils, jars of various pickled delights, bulk tea and spices and, of course, bags of fragrant, nutty beans to take home; the French roast is particularly fine.

Once you’re properly caffeinated, it’s time to sightsee. Whether by bicycle or by car (or by foot if you’re intrepid), a trip along the winding coastline is mandatory. Photo-ops of sweeping harbor vistas, backlit by fiery foliage, wait around every bend of the road—including the aforementioned Bush compound. Snap a pic for the folks but don’t attempt an up-close look; two imposing black SUVs sit in the sprawling estate’s drive, even in the offseason. Never mind, as political buffs can get a fix at the Ramp, a quirky, ramshackle dive that offers unparalleled views of Cape Porpoise Harbor. Order a lobster roll and a bowl of chowder (both authentic and tasty) and post up at the bar to ogle the restaurant’s many pieces of flair—signed Patriots helmets, vintage Sox pennants, old Bush and Kerry campaign posters, a splintered Boston police barricade, a framed black-and-white photograph of George and Barbara and, in the corner, a leering piñata caricature of one Donald J. Trump. Not a surface or raw wooden beam is left uncovered.

One could easily linger over pints all day, watching the sun dip below the tree line and paint the harbor with even more vivid brushstrokes, but there’s more to see—and to drink. Stop back at the inn for a warm sweater and teatime in the drawing room. Sip some Earl Grey or grab a snifter of good brandy from one of two large glass tumblers that guests are welcome to tap at their discretion. Thusly fortified, make your way back into town, this time to Federal Jack’s, a brewpub that sits above the Kennebunkport Brewing Company, a seven-barrel brewery from which the now Portland-based Shipyard Brewing Company was born. Peek in the open windows at the beer brewing in large metal vats and read the placards that serve as a DIY brewery tour and explain KBC’s brewing process—all to better your understanding of what you’ll be quaffing upstairs, where the hopping Federal Jack’s offers seven drafts. Order the Old Thumper, a 1985 British Grand Champion bitter ale, or a flight to sample them all.

If vino is more to your taste, end your afternoon at Old Vines Wine Bar, a chic purveyor of offbeat wines from small producers around the world that wash down tasty nibbles (spring for two orders of the fried shishito peppers with Hawaiian sea salt and Japanese mayo). Pro tip: There’s a nightly happy hour from 5 to 6 pm that grants 50 percent off any 6-ounce pour. If the weather permits, take your wine outside to recline in one of the Adirondack chairs or at one of the picnic tables that surround a blazing fire pit. Make friends with the other sweater-bundled drinkers around the fire: You’ll be seeing them later for a nightcap at Ryan’s Corner House Irish Pub & Restaurant, a no-frills dive that serves as your last stop before you sink into sleep beside your crackling in-room fireplace back at the White Barn, a snifter of brandy glowing warmly on the bedside table.

Traveler’s Checks      

-Feel the heat at Flaming Gourmet, which stocks salsas, jams, spreads, dips, mustards and a staggering wall of hot sauces that includes some of the hottest in the world—One Fuckin’ Drop at a Time Hot Sauce and El Yucateco’s chile habanero sauce among them.
-Even more breathtaking seaside vistas can be found a 25-minute drive away (it’s worth it) at Ogunquit’s Marginal Way, a 1.25-mile walking trail atop cliffs that line the southern Maine coastline.

Coffee Roasters of the Kennebunks, 163 Port Road, Kennebunk (207-967-8304) coffeeroastersofthekennebunks.com; Federal Jack’s Restaurant & Brewpub, 8 Western Ave., Kennebunk (207-967-4322) federaljacks.com; Flaming Gourmet, 28 Dock Square, Kennebunkport (207-967-8825) flaminggourmet.com; Marginal Way, 23 School St., Ogunquit (207-641-2200) marginalwayfund.org; Old Vines Wine Bar, 173 Port Road, Kennebunk (207-967-2310) oldvineswinebar.com; The Ramp Bar & Grill, 77 Pier Road, Kennebunkport (207-967-8500) pier77restaurant.com; Ryan’s Corner House Irish Pub & Restaurant, 17 Western Ave., Kennebunk (207-967-3564); White Barn Inn, 37 Beach Ave., Kennebunk (207-967-2321) whitebarninn.com