When maple trees are at peak fall color, their beauty will take your breath away! In New England, this is traditionally within the first two weeks of October. If you’re dreaming of the ultimate leaf-peeping adventure, there’s no better place than New England. Crisp mountain air, winding scenic roads, charming towns, and fiery fall colors all come together to create a trip you’ll never forget. This season is short but spectacular, planning ahead & dressing appropriately (including smart packing) is the secret to making the most of it. Here’s our favorite itinerary — one that blends a little history, scenic beauty, and a few delicious stops along the way. Start in Boston, MA Fly into Boston to begin your journey. Spend a little time exploring some of the city’s highlights before heading north — we love strolling the Boston Freedom Trail, Faneuil Hall and Quincy Market, window shopping along Newbury Street in the Back Bay or grabbing a cozy meal in the North End. Then, get a good night rest, grab breakfast at one of our favorite spots – Flour Bakery and Café. Now you’re ready to hit the road with provisions in hand. Woodstock, VT The storybook town of Woodstock is one of the prettiest in Vermont. Check into the classic Woodstock Inn, then wander Main Street’s boutiques, galleries, and farm-to-table restaurants. Don’t miss the Woodstock Farmers Market, where you can stock up on picnic-ready salads, local cheeses, cider, crackers, and even a can of Vermont’s famed Heady Topper IPA for later. Hanover, NH & Norwich, VT From Woodstock, make your way to Hanover, New Hampshire, home of Dartmouth College. The historic campus is charming in fall, with golden leaves crunching underfoot. Just across the Connecticut River lies Norwich, VT, where the King Arthur Baking Company Store awaits. It’s a baker’s paradise — pick up fresh bread, baking mixes, or a few sweet treats for the road. Warren, NH to Lincoln, NH Next, drive along the scenic Sawyer Highway (Route 118) to Lincoln. The winding roads are lined with fiery red, orange, and gold leaves, offering some of the prettiest views in the state. Lincoln, NH & the Kancamagus Highway Lincoln is the gateway to the legendary Kancamagus Highway (Route 112) — a 60-mile stretch of pure autumn magic. This drive is a must-do, with multiple places to stop and soak in the scenery: Sabbaday Falls – a picturesque waterfall perfect for photos. Lower Falls – an easy, family-friendly stop. Albany Covered Bridge – a historic 1858 bridge over the Swift River. Fadden’s General Store & Sugarhouse (North Woodstock) – award-winning maple syrup and local charm. Conway, NH to Mt. Washington From Conway, continue north toward Mt. Washington. Along the way, you can stop for an easy one-mile hike to Diana’s Baths Waterfall in North Conway. Once at Mt. Washington, stay at the historic Omni Mt. Washington Hotel, where sunset drinks on the porch are a tradition. Adventurous travelers can hike the mountain, but if you prefer a less strenuous option, take the Cog Railway or drive the Auto Road to the summit. (Book tickets in advance — these fill quickly during foliage season!) Return to Boston From Mt. Washington, make your way back to Boston, via the White Mountain Highway and Interstate 95 in Portsmouth. If time allows, we like to stop in Kittery at Bob’s Clam Hut for some clams or a lobster roll before heading back to Boston and closing the loop on your fall adventure. 🍂 Travel Tip: Book your hotels early — New England fills up quickly in October. The first half of the month is usually peak season, but exact timing varies each year. With a little planning, you’ll be rewarded with some of the most spectacular fall foliage in the world.
Travel in Style Without the Stress…
Our Ultimate Capsule Wardrobe Guide There’s something about hitting the road (or the skies) that brings out the best in us—new adventures, unforgettable memories, and of course, the opportunity to travel in style without the stress. The Shookhill, travel calendar is packed for the rest of the year. Do you have fall travel plans? If not, find inspiration in our travel section. We are also working on some great fringe season itineries for you. From meandering along the rocky coastline of Maine and leaf peeping in New England to exploring a few new european destinations in Greece, and Italy, —before wrapping up the year in festive flair at the Christmas markets in France and Germany. To do all this, we need to stay organized, comfortable, and effortlessly chic. This requires thoughtful planning, organization, and a capsule wardrobe. That’s where our Travel Style Guide comes in. We created this capsule wardrobe guide for every season to take the guesswork out of packing. The secret? Capsule Wardrobe Packing for every season! Curating a collection of versatile, layerable, mix-and-match pieces that work across climates and cultures. Think: neutral tones, breezy fabrics, and easy-to-accessorize basics. What’s In Our Bag? It’s the question we get asked most often—and we dedicated and entire post to answering your questions. Included are the travel staples we never leave home without, comprising of comfortable footwear for city strolls, our absolute favorite bag, organizer insert and our go-to day bag basics that have saved the day on numerous occasions. We’ve also got a few tricks up our sleeve: Pack by outfit, not item. Choose clothes that can be worn at least twice (and are interchangeable with a variety of outfits). Roll, don’t fold. Use packing cubes for organization Leave space for local finds & souvenirs (we look for easy to pack items that will remind us of our trip and help share our travel memories). This wardrobe system makes it simple to get dressed while on the go—whether we’re exploring ruins, sampling tapas, or toasting with glühwein in Strasbourg. Planning a trip soon? Check out our Travel Style Guide and our new “What’s in My Bag” feature for inspiration. Wherever you’re headed next, let us help you travel in style—without the stress.