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.
