10 Quintessential Fall Weekend Trips

Shortening days, comfy sweaters, steaming mugs of warm apple cider: Some things are so quintessentially fall that, despite the promise of snowy days to come, we just can’t wait to partake. Autumn is the ideal time for weekend trips both urban and rustic. Check out our 10 favorite fall destinations and then plan your own cozy escape.

Mount Washington, New Hampshire

The octet of villages in New Hampshire’s Mt. Washington Valley would scream “fall in New England” … if screaming weren’t completely out of character for the area’s tranquil spirit. While the region is known for snow sports and world-class skiing later in the season, it’s also brimming with autumnal activities. From leaf peeping along the Appalachian Trail to pick-your-own pumpkin patches and apple orchards, there’s something for everyone along the area’s winding byways. In North Conway, take a ride in historical Pullman cars on the Conway Scenic Railroad before stopping at one of the many nearby outlets … you know, for your new fall wardrobe.

Where to Stay: Little inns abound in this region, but The Wentworth (with its AAA Four-Diamond dining room) is a particularly polished but cozy option in Jackson Village that offers several packages for fall getaways, with low off-season rates.

Nashville, Tennessee

Stumbling upon a musical performance in Nashville is as inevitable as the changing of the seasons. Artists and travelers alike flock to Music City each fall for a slate of festivals, headliner shows, and the opening of the theater and opera seasons. Take your pick of the area’s many pumpkin patches, corn mazes, and farmers’ markets for a seasonal Tennessee bounty, or embark on the Tennessee Central Railway Museum’s 4.5-hour Oktoberfest Excursion for live music, beer, and food throughout the highlands of Tennessee. If you want to sneak in some leaf peeping, peak colors occur around the third and fourth weeks of October.

Where to Stay: Most major hotel chains have outposts in Nashville; check out seasonal deals from Hilton and Loews. Also be sure to dig through the offerings from VisitMusicCity.com, where seasonal hotel packages can be music to your ears.

Santa Fe, New Mexico

Santa Fe continually ranks among Travel + Leisure‘s top places to catch some peace and quiet, and natives contend that September is the best time to visit this southwestern city. That’s when the crowds have thinned but the weather remains warm and welcoming. Catch a little R & R yourself this fall, Santa Fe-style. Witness the aspen leaves turning a brilliant gold as you stop at roadside stands brimming with late-harvest corn and roasted green chiles. (Try the region’s signature veggie in all its forms at the Santa Fe Wine & Chile Fiesta or October’s interactive Harvest Festival.) And when too much activity makes you weary and worn, check into one of the area’s many renowned spas for a relaxing and renewing treatment.

Where to Stay: Santa Fe Sage Inn has a list of packages for travelers coming to the city, plus complimentary continental breakfast and free Wi-Fi access. The Santa Fe Convention and Visitors Bureau lists more discounts on accommodations, activities, excursions, and dining here.

Mackinac Island, Michigan

This historical island is a classic Midwestern destination: a Victorian-era getaway on Lake Huron, replete with gingerbread houses and horse-drawn carriages (and largely without the pesky annoyance of motor vehicles). Mackinac Island has its last hurrah in October, when the days get chilly but the island reveals its more peaceful side: quiet but alive with fall color, festivals, and events. Experience the thrill of Historic Mill Creek Discovery Park, where a zip-line and canopy walk wind through cedars high above the ground. Bike across the famous Mackinac Bridge or picnic on the shores of the Straits of Mackinac, where the Michigan and Huron lakes merge. Or simply stay in and enjoy a slate of activities, from the Mackinac Island Halloween Weekend (October 22-24) to a cozy murder-mystery weekend at the iconic Grand Hotel.

Where to Stay: Fall in Mackinac Island means hotel discounts, generally of around 15 percent or more. The Grand Hotel currently features a Fall Bed and Breakfast Package from $331 per person per night. Find more vacation packages on Mackinac Island’s tourism site, including free admission to local sights and activities, AARP specials and deals for AAA Travel members, and special rates on stays at the island’s many historical inns.

Boston, Massachusetts

Locals maintain that fall is the best time to visit this classic and collegiate New England getaway: Both Boston and its sister city Cambridge are alive with new students, and the heat has dissipated downtown. Visit the scenic Boston Common and the Public Garden, where trees explode in fiery reds, oranges, and yellows; stroll Cambridge’s grassy, tree-lined Harvard Yard; or be gently pushed along the Freedom Trail by autumn breezes while on a tour (complete with a guide in authentic colonial garb). Brisk October brings the iconic two-day Head of the Charles Regatta, when some 9,000 athletes take to the Charles River and more than 300,000 spectators take to its banks. Baseball fans can catch a post-season Red Sox game at historic Fenway Park.

Where to Stay: Accommodations can be pricey in this urban destination, especially during the Head of the Charles and other seasonal events. Check online travel agencies (OTAs) for up-to-date rates and last-minute savings. For a luxe fall-themed stay, check into boutique XV Beacon to take advantage of their Fall Into Fifteen package now through December 21st, where a stay of 2-nights or more earns you 15% their best available rate per night.

Hudson River Valley, New York

New York’s Hudson River Valley is a picturesque escape 90 minutes from Manhattan, replete with rolling hills, cascading waterfalls, and sleepy Victorian villages occupied by grand manses. The oldest wine-making and grape-growing region in the country is saturated with color every autumn, and its various wine tours welcome those looking for a taste. Sip a few varietals before heading to the Culinary Institute of America in Hyde Park to sample dishes at one of the five student-run restaurants on-site; beautiful Valley views complement the meal. Finish with a walk (or bike ride) 212 feet above the Hudson River on the Walkway Over the Hudson state park. Opened in 2009, this pedestrian bridge offers postcard-worthy foliage, plus picnic benches perfect for a lunch of apples and cheese sourced from local farms.

Where to Stay: Mohonk Mountain House in New Paltz has numerous fall-centric specials, including up to 30% certain midweek dates now through November.

Eastern Shore, Maryland

A peninsula buttressed by the Chesapeake Bay, the Eastern Shore has long been a summer favorite for East Coasters who hit the outdoors for world-class boating and bird-watching. But autumn is also a worthy time to visit this seaside region’s small towns for their mild weather and fall festivals. In Cambridge, the Blackwater National Wildlife Refuge (which stretches over 25,000 acres) acts as a sanctuary for endangered waterfowl; the area is best explored from mid-October through mid-March. Along the Choptank River, Cambridge itself is a resurgent small town with a burgeoning artsy vibe; check out its galleries and events here. (Spoiler: Oysters and hot sauce may be involved.) Experience quaint St. Michaels during the Fall Into St. Michaels festival before exploring its quirky gift and antique shops. For some bigger-town excitement, Ocean City beckons with sandy beaches and, during the fall season, a boardwalk largely free of crowds.

Where to Stay: The Eastern Shore has plenty of accommodation options, but bed-and-breakfasts often provide the best value, especially in the off-season. If a larger hotel is more your speed, the Hyatt Regency Chesapeake Bay offers discounts up to 10% for members. Explore the flood of fall freebies and accommodations deals on the Ocean City tourism website as well.

Shenandoah Valley, Virginia

A proper mix of eclectic downtowns, mountain resorts, and natural wonders (think limestone caverns) make Virginia’s Shenandoah Valley a year-round destination. But fall brings out the region’s true colors. Take a spin through the Blue Ridge Parkway on the eastern edge of the valley or motor the 105-mile Skyline Drive, which features 75 scenic outlooks for admiring nature cloaked in its scarlet, maroon, and golden finest. Visit the Marker-Miller Orchards for PYO apples, or browse the market for other fall goodies, from pluots to pears to prunes. Downtown Lexington is brimming with antique shops, galleries, and food purveyors where you can grab Amish goods and local confections.

Where to Stay: In Lexington, the Brierley Hill Bed and Breakfast is a TripAdvisor-approved stunner nestled in the region’s rolling meadows; find a number of romantic packages from their Honeymoon bundle to the Wine and Cheese package. For those looking to rough it (but not really), the authentic timber-framed cabins at Shadow Mountain Escape are a charming and eco-friendly home base on the border of Shenandoah National Park.

Stowe, Vermont

Stowe may be another one of New England’s winter hot spots—er, cold spots—but fall is chock-full of events that draw tourists to this almost-250-year-old mountain village. The Stowe Foliage Arts Festival (October 8–10) brings together 150 craftspeople, artists, and specialty-food makers—and the usual throngs of fall tourists—under a canopy of colorful leaves. Visit Foliage Central on GoStowe.com for itineraries, kids’ activities, and up-to-the-minute news on the leaf situation.

Where to Stay: Stoweflake Mountain Resort & Spa is offering savings between 10 and 20 percent with their Book Early, Save More package. The Sun & Ski Inn and Suites features low rates in its guest rooms, suites, and full-sized condos plus 15 percent off any night stay with travel dates between November 1st and December 17th. Check GoStowe.com for a current list of deals.

Columbia River Gorge, Oregon

This is a nature lover’s state of grace. The mighty Columbia River carves a twisting path through the Cascade Mountains, leading to waterfalls, rocky beaches, and charming cabins along its wide canyon. Take in the stunning 620-foot Multnomah Falls along the Historic Columbia River Highway, or follow the paved ribbons of hiking trails. Explore these geological wonders your way: Trek, bike, windsurf, whitewater raft, or merely sit for a while and soak in the crisp fall air. The weather is brisk, and while the water may be frigid for all but the most adventurous, the area’s countless craft breweries and pubs beg visitors to pop in for a pint and a warm-up with views of the trees’ explosive wardrobe change.

Where to Stay: Statewide, camp in a number of recreation sites and state parks for nominal rates, or rent a cabin via VRBO. Redefine “roughing it” at Carson Ridge Luxury Cabins; look into seasonal, romantic, and adventure-themed specials on the property’s website.

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