According to Turo’s 2026 USA Road Report, travelers ages 46 to 60 are more drawn to scenic drives and small-town escapes than other generations. In fact, 78% of Americans surveyed are planning visits to picturesque destinations, while Gen X specifically favors the kind of trips practically made for fall: winding roads, charming downtowns, historic inns and plenty of places to pull over for apple cider doughnuts.
For Gen Xers entering the empty-nester era, there’s another perk: You can finally match the car to the trip instead of the carpool. Through Turo, travelers can swap the everyday SUV for a rugged Toyota 4Runner, adventure-ready Subaru Outback or even a convertible that makes a scenic autumnal drive part of the vacation.
So, where should you point the GPS? Here are five small-town escapes tailor-made for a fall road trip.
Related: 20 Best Fall Foliage Trips for Fall Colors Near You
5 Small Towns Worth Hitting the Road for This Fall
Old Saybrook, Connecticut
An aerial shot of Saybrook Point Resort & Marina in Old Saybrook, Connecticut.Saybrook Point Resort & Marina
Follow in Katharine Hepburn’s footsteps in the Connecticut shoreline town she called home, where fall means crisp waterfront walks and foliage-framed drives along the coast. Visit the Katharine Hepburn Museum at The Kate, browse the quaint shops and galleries on Main Street, then check into the charming Saybrook Point Resort & Marina, perched where the Connecticut River meets Long Island Sound.
The family-owned resort makes an especially cozy fall base with a full-service spa, waterfront dining, historic guesthouses and newly renovated rooms filled with maritime touches. For an extra dose of old-school New England, make the short drive to Essex and stop by The Griswold Inn for drinks, dinner and one of its legendary Monday-night sea shanty sing-alongs.
Woodstock, Vermont
Covered bridges, white-steepled churches, farm stands and mountains blazing red and gold make Woodstock almost suspiciously perfect in autumn. Wind your way through the countryside, stopping at Middle Covered Bridge and Sleepy Hollow Farm when the foliage demands a photo, then browse the boutiques and galleries around the village.
Bed down at Woodstock Inn & Resort, where you can cozy up by the fire after a day outdoors, or head to nearby Billings Farm & Museum for a dose of quintessential Vermont farm life. Before leaving town, swing by Sugarbush Farm to stock up on maple syrup and cheese, because no New England fall road trip should end without edible souvenirs.
Kennebunkport + Ogunquit, Maine
White Barn Inn’s celebrated AAA Five Diamond restaurant in coastal Maine.White Barn Inn, Auberge Collection
Make White Barn Inn, Auberge Collection your luxe home base for a southern Maine leaf-peeping weekend, then cruise the coast to Perkins Cove in Ogunquit, food-crawling its famous seafood haunts like Barnacle Billy’s, Footbridge Lobster and Jackie’s Too. Wander the working harbor and take a fall stroll along the Marginal Way before retreating to the inn for a cozy evening.
Their original tavern, which dates back to 1973, is especially fitting for an autumnal pastime: a private wine-and-cheese tasting personally curated by head sommelier Ann. Come fall, the floor-to-ceiling windows frame oversized mums, gourds and changing leaves, making an already charming experience feel tailor-made for the season.
Stockbridge, Massachusetts
Norman Rockwell country practically wrote the book on nostalgic New England road trips. Drive through the Berkshires at peak foliage, visit the Norman Rockwell Museum, wander Stockbridge’s postcard-worthy Main Street, and make time for one of the area’s historic estates or gardens.
Make a stop at Naumkeag, where the historic Gilded Age estate and gardens are especially pretty against the Berkshires’ changing leaves, or head to Berkshire Botanical Garden for an autumn stroll. When you’re ready to warm up, duck into one of Main Street’s cafés before taking the long way back to your hotel. After all, this is one road trip where getting a little lost among the foliage is kind of the point.
Hudson, New York
The Maker Hotel in Hudson is ideal for a fall foliage getaway.The Maker
For Gen Xers who want their small-town escape with a little more edge, head for the Hudson Valley. Spend the day antiquing and gallery hopping along Warren Street, break for cocktails and a great dinner, then use Hudson as a jumping-off point for scenic drives through the surrounding countryside.
The Maker Hotel, a moody, design-forward hideaway dripping in jewel tones, antiques and plenty of old-world romance, is an ideal home base for the weekend. Lean into the mystical fall mood with a private tarot card reading before grabbing cocktails by the fire. It’s basically autumn escapism in hotel form.
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