On the Road Again - Colorful Road Trip Itineraries to Celebrate Fall

Sometimes the best adventures are those where the open road itself is the destination, and lucky for us, there is so much natural beauty to be seen on a classic American road trip. Now that Labor Day has passed, if the unofficial arrival of autumn has you craving a change of scenery, you’ll enjoy discovering the colorful road trip itineraries below. Pack your coziest sweaters and create your perfect playlist — I'll take care of the rest. Soon you'll spend your days cruising remarkably scenic byways saturated in brilliant autumn hues. You'll uncover hidden gems, flavorful pitstops, lively seasonal events, and the finest accommodations along the way. Don’t wait until the last leaf turns to get in touch. Your idyllic autumn adventure awaits!

GET ON THE ROAD TO NEW ENGLAND

EXPLORE BOSTON TO BAR HARBOR: THE REGION'S MOST SCENIC DRIVE

A New England road trip during peak fall is as all-American and enticing as a freshly baked apple pie. After exploring the historic streets of Boston, this classic road trip will take you on a sublimely scenic journey to explore historic small town main streets and roadside restaurants serving the tastiest sea-to-table eats. Cruise up I-95 to Portsmouth, New Hampshire then switch to coastal Highway 1 for the slower scenic route. Spend a few days exploring boutiques and galleries, microbreweries, and picture-perfect lighthouses in Kennebunk and Portland, and enjoy VIP treatment while staying in a private cottage at White Barn Inn & Spa. Make your way up Maine's beautifully quaint midcoast, and stretch your legs on seaside nature walks en route to Bar Harbor, your base for exploring the kaleidoscope of fall colors you'll find on the 27 stunning miles of historic roads through Acadia National Park.

GET ON THE ROAD TO THE ROCKIES

DISCOVER COLORADO'S SAN JUAN SKYWAY & MILLION DOLLAR HIGHWAY

If your favorite time of day is golden hour, head to the Colorado Rockies in autumn where golden hues last the whole day through thanks to aspen leaves turning vibrant shades of amber. There are countless Rocky Mountain road trips, but if you've never driven the San Juan Skyway and Million Dollar Highway in southwestern Colorado, it's time you experience the jaw-dropping panoramas and spectacular foliage as you wind your way through San Juan and Uncompahgre National Forests. This 233-mile mountain adventure passes by the charming mountain towns of Durango, Dolores, Telluride, Ridgway, Ouray and Silverton. Don't miss soaking in the nearby hot springs and taking a short detour to Mesa Verde National Park, where you can explore ancestral Puebloan cliff dwellings. Madeline Hotel in Telluride is the ultimate luxury basecamp to explore this alpine region.

GET ON THE ROAD TO THE BLUE RIDGE PARKWAY

WIND YOUR WAY FROM SHENANDOAH TO ASHEVILLE

Named "America's Favorite Drive" for good reason, the Blue Ridge Parkway winds its way through the southern Appalachians and stuns at every bend in the road. Stretching 465 miles between Shenandoah National Park in the north and Great Smoky Mountains National Park in the south, this mountain region is a natural paradise of forested peaks and sun-dappled valleys painted the prettiest shades of the season. With a speed limit of 45 mph, you'll be happy this roadway encourages you slow down to enjoy plenty of outdoor adventures and savory pitstops along the way. Spend a few luxurious days at Primland Resort, a 5-star mountain estate on your way to Asheville. When you arrive, a visit to the exquisite Biltmore Estate is a must — as is a night out to celebrate your adventure and enjoy live bluegrass music over a locally brewed pint.

GET ON THE ROAD TO WINE COUNTRY

SIP YOUR WAY FROM SONOMA TO MENDOCINO

Northern California’s Sonoma and Mendocino counties stretch from the rolling hills of wine country to striking shores of the Pacific, and the season of harvest is primetime for exploring this picturesque region. Country roads lead you over golden hills, along lush river valleys, and through ancient redwood groves. Visit charming villages, and experience sublime farm-to-table dining and acclaimed vineyards along the way. If you prefer to explore the countryside on two wheels instead of four, enjoy complimentary bike rentals when you stay at the Montage Healdsburg and a $100 spa credit (my compliments!) to revitalize after a day of adventure.

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