There’s something magical about fall in the Northeast. The season feels alive—vivid leaves paint the landscape in fiery reds, golden yellows, and deep oranges, while the crisp air invites you to wander winding country roads, windows rolled down, hot cider in hand. For me, autumn is about more than the scenery; it’s about renewal. It’s cozying up in rustic inns, savoring the scent of wood smoke, and chasing the fleeting wonder of “peak foliage.” It’s a time when every drive, every small town, and every stop along the way feels like an adventure.

Connecticut’s Golden Charm

When autumn arrives, Connecticut is my first destination. With its postcard-worthy villages and rolling hills bursting with color, it’s the perfect place to experience the season’s beauty. At the heart of it all sits the Auberge Mayflower Inn & Spa, an elegant retreat where you can fully immerse yourself in the spirit of fall. Whether you’re wandering the grounds, sipping mulled cider by the fire, or simply gazing out at the ever-changing trees, it’s the kind of place that makes you slow down and savor the moment.

Beacon: The Hudson Valley’s Creative Soul

A true autumn road trip wouldn’t be complete without a journey up to the Hudson Valley, where some of New York’s most charming towns come alive this time of year. Beacon is one of those can’t-miss stops—a vibrant town that balances culture, food, and natural beauty.

Beacon’s dining scene is worth the trip alone. For a refined experience, book a table at The Roundhouse, where floor-to-ceiling windows overlook the river and locally sourced dishes feel both comforting and elevated. For a more casual vibe, wander into Beacon Bread Company, a cozy café brimming with fresh pastries, artisanal breads, and the smell of coffee that seems to hug you the second you walk in. If you happen to visit on a Sunday, don’t miss the Beacon Farmers Market, where local vendors showcase everything from seasonal produce to handmade goods.

Millbrook: A Treasure Hunter’s Dream

Head a little northeast, and you’ll find Millbrook, a paradise for vintage lovers. This town is like stepping into a well-curated time capsule, each shop filled with pieces waiting to be rediscovered. The Millbrook Antique Mall is a favorite stop of mine—a treasure trove of finds ranging from unique home décor to heirloom jewelry. Even if you’re not on the hunt for anything specific, browsing the shelves feels like an adventure in itself. Add to that the town’s storybook charm, and Millbrook becomes the kind of place you’ll want to linger.

More Antique Havens to Explore

Of course, no autumn road trip would be complete without more antique stops scattered along the way. Here are a few more towns to bookmark if you love the thrill of discovering something with history:

• Litchfield, Connecticut – This historic town is renowned for its colonial architecture and array of antique shops. Favorites include South Street Antiques, Bradford House Antiques, and Jeffrey Tillou Antiques, each offering its own flavor of timeless treasures.
• Woodbury, Connecticut – Often hailed as the “Antiques Capital of Connecticut,” Woodbury is a must for serious collectors. At Farmhouse Antiques, you’ll find everything from finely crafted furniture to vintage jewelry. And don’t skip the Main Street Antique Center—the selection is vast, and the prices might surprise you.
• New Milford, Connecticut – This town’s streets are lined with antique shops full of collectibles, artwork, and vintage clothing. The real gem, however, is the Elephant’s Trunk Flea Market, open on Sundays. It’s a vibrant, outdoor shopping experience where unique finds practically beg to come home with you.
• Kent, Connecticut – Known for blending the old and the new, Kent is home to both antique shops and contemporary galleries. RT Facts is a standout, with its beautifully curated mix of antiques and art that feels more like a design destination than a shop.

Why Fall Upstate Feels Like Magic

What keeps me returning to these towns year after year isn’t just the antiques or even the food (though both are incredible). It’s the feeling of discovery woven into the season itself. Autumn reminds us to pause—to breathe in the crisp air, to marvel at the changing leaves, and to delight in the small joys of wandering. Each town offers its own character, but together they create a tapestry of experiences that make a Northeast fall road trip unlike any other.

So, if you’ve been waiting for the perfect excuse to escape the city or your everyday routine, let the season be your guide. Pack a cozy sweater, cue up your favorite road trip playlist, and set off on an autumn adventure. The fiery landscapes, charming villages, and hidden treasures of the Northeast are waiting—and trust me, they’re even more breathtaking in person.