5 Best Cities for Fall Travel

Add one of these fun cities to your fall travel itinerary.

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As summer winds down, most folks put away their suitcases, patiently waiting for the following summer's vacation. Poor people. Why sulk in sadness when you can plan an autumn road trip instead? Fall can be a blissful time to visit many cities; crowds diminish, temperatures are comfortably cool (but not cold), and autumn- and Halloween-themed festivals keep locals and travelers occupied. Seasonal sports, like football and hockey, also kick into high gear in the fall, luring fans into stadiums and sports bars in cities where passions run high. It's also the season of spookiness, with ghost tours celebrating Halloween horrors. So start prepping for cool weather fun with our picks for America's best cities for fall travel.


New England takes the nation's prize for most glorious autumn leaf-peeping opportunities, especially in Boston. Hop aboard one of the many bus or boat tours in downtown Boston to explore nearby New England towns and regions like Cape Cod or New Hampshire. Or simply take a stroll along the Charles River, where colorful autumn leaves line the river banks.

Every October, you can also see rowers cut through the waters in slender skiffs. One of Boston's most popular events, the Head of the Charles Regatta draws more than 8,000 athletes to the city to compete in what is the world’s largest two-day rowing race. In the autumn, Boston's football, hockey and basketball teams start to heat up, too, as students return to the dozens of metro area colleges. Grab tickets to a Patriots or Bruins game — football and hockey reign supreme this time of year.

What to Do in Boston This Fall

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Boston is the ideal fall getaway. Flights are cheaper, and its quaint charm will appeal to every kind of traveler.

Maybe it's the picturesque location, situated right on the Charles River and Atlantic Ocean. Maybe it's the old world cobblestone streets and rich history. Maybe it's the pleasant temperatures: not too hot, not too cold. Or, maybe, it's the impossibly fresh lobster and shellfish. For me, all of the aforementioned reasons (and more) set Boston apart as the perfect long weekend destination.

Clearly, I fell head-over-heels in love for Boston. Here are a few reasons you will, too.

Photo By: Molly Miller

It's Walkable

Boston has beautiful fall weather, so take advantage of it!

But, public transportation is also very easy to use. The T, as locals call it, will quickly take you wherever you want to go in the city. I stayed with my friend in Arlington, and it took about 30 minutes to get downtown. Once you're in the city center, here are a few walking routes I recommend.

Photo By: Molly Miller

Route 1

Follow the Freedom Trail. This brick path will take you past every notable historical site in the city, including Bunker Hill, Paul Revere's house and the Old North Church. Start at Bunker Hill, working your way down across the Charles River. (Tip: If your legs need a break from climbing 294 steps at Bunker Hill, take a ferry to Long Wharf for fantastic views of the Boston skyline.) Follow the trail to the Old North Church, down to Paul Revere's house in the Italian district, through Quincy Market to the Old South Meeting House and, finally, to the Boston Common. Cheers fans will be happy to know that the iconic bar is located nearby on Beacon Street.

Photo By: Molly Miller

Route 2

Start at the intersection of Newbury Street and Massachusetts Avenue for shopping and sightseeing. Boylston Street (one block over from Newbury) takes you past the Boston Library, Boston Marathon Finish Line and Trinity Church. Both Boylston and Newbury run into the Public Garden, where weeping willow trees dance in the wind over a pond. After a stroll through the Public Garden, head into Beacon Hill via Charles Street for a taste of old Boston.

Photo By: Molly Miller

Route 3

Explore the burgeoning art district near the South End, SoWa Art + Design District. Here, you'll find open markets, hip restaurants, art galleries and festivals. Then make your way through Chinatown, towards the Boston Tea Party Ship and Museum, and on to Harpoon Brewery to close out the night.

Photo By: Molly Miller

There's Something for Everyone

For nerds, Cambridge houses the esteemed universities MIT and Harvard. Explore the campuses, libraries, bookstores and museums in the area for a day of educational fun. You'll get a real taste of campus-life in the fall when school is in session.

Photo By: Molly Miller

Newbury Street Boston

Shopping fanatics will love Newbury and Boylston streets for their high-low mix of stores. Here, you'll find everything from Madewell and H&M to Balenciaga and Chanel. It's the perfect spot to get all of your fall (and holiday!) shopping done.

Foodies and beer geeks can take advantage of Boston's many breweries, like local favorite, Trillium, and inventive restaurants. If restaurant and brewery hopping doesn't keep you busy, attend one of Boston's many food festivals that take place in September and October, like the Copenhagen Beer Festival.

Photo By: Molly Miller

Outdoor enthusiasts can find enjoyment in the urban jungle thanks to the Charles River. Rent a kayak to see Boston by boat or borrow a bike to explore the city's many greenways. Bostonians are very active, so you won't feel out of place taking a jog through its neighborhoods.

Photo By: Molly Miller

Artsy types will feel right at home in SoWa, with its galleries, artisan markets, shared creative spaces and fresh, organic food options. The Opera House, Museum of Fine Arts and Institute of Contemporary Art all warrant a visit. Plus, tons of new exhibits debut at museums in the fall.

Photo By: Molly Miller

Families will enjoy the Museum of Science or New England Aquarium. Grab ice cream afterward near the Greenway Carousel, then saunter over to Quincy Market to see street performers and shop from local vendors. There's also an adorable tribute to the famed children's book "Make Way for Ducklings" in the Public Garden.

Photo By: Molly Miller

In addition to the Freedom Trail, history geeks should also visit the Boston Library, USS Constitution Museum, the Isabella Stewart Gardner Museum and Old State House. These usually packed tourist spots will be almost empty in the fall.

Photo By: Molly Miller

It's Gorgeous

Between the cobblestone streets, historic sights, numerous parks, waterfront views and brownstones with luscious planter boxes, Boston's beauty can't be denied. If you go at the perfect time, you'll catch stunning fall foliage, too.

Photo By: Molly Miller

For beautiful river views, the Esplanade can't be missed. Situated just a few blocks from the Boston Common and Boylston Street, this public park is a popular spot for locals during summer and fall. Rent a sailboat for a day on the river or sit back and watch them sail by, coffee in hand from the Charles River bistro.

Photo By: Molly Miller

Gotta fuel up for the long winter, right?

Mario Batali's Eataly is a MUST. This marketplace-slash-eatery offers fresh seafood, house-made cheeses, a meat counter, wine shop, local produce and 14 spots to grab a bite. Plan to spend at least two hours here.

In Cambridge, try the acclaimed tapas restaurant Little Donkey, the Border Cafe for a fun atmosphere with Tex-Mex and Cajun food, and grab a cannoli from famed Mike's Pastry.

Photo By: Molly Miller

Like seemingly every other major city in the U.S., Boston loves brunch. If you're staying near Arlington (like I did), Rosebud Diner serves up homemade doughnuts and incredible eggs benedict. In the city center, Beehive is a local favorite as well as Abe & Louie's or The Gallows in the South End.

Photo By: Molly Miller

Pizza and seafood reign supreme here. Check out popular seafood spot Neptune Oyster for mouth-watering lobster rolls and, of course, oysters, Legal Sea Foods for an upscale experience or Yankee Lobster Co. for seaside views. Regina Pizzeria, Za, Area Four, Ernesto's or Picco serve up delicious slices of pie, all with their own twist.

For Asian fare, try the Thelonius Monkfish in Cambridge or Gourmet Dumpling House, Hei La Moon and Shojo Restaurant in Chinatown.

Photo By: Molly Miller

Day Trips Are Very Doable

Small, picturesque coastal towns lie less than two hours away from the bustling city. Halibut Point in Rockport is a lovely place to spend the afternoon. Pack a picnic and watch the waves crash against the craggy shore. Then, grab dinner and browse local shops in idyllic Rockport.

Photo By: Molly Miller

Newport, Newburyport, Cranes Beach, Portsmouth and Martha's Vineyard also make for great overnight stays or day trips. Even better? Tourism dies down in the fall, so, you'll virtually have these towns to yourself.

And don't forget about apple picking and pumpkin patch visits! Massachusetts is ripe with apple orchards, vineyards and pumpkin patches.

Photo By: Molly Miller

Savannah, Ga.

Savannah, Georgia

Savannah, Georgia

Photo by: Andrew Ciscel, Flickr

Andrew Ciscel, Flickr

Who wouldn't want to visit one of America's most haunted cities in autumn? Savannah's spooky factor and popular ghost tours are reason enough to visit this historic city any time of year, but the town's aura feels even more ominous with Halloween on the horizon. Fall also brings a medley of events and festivals to Savannah, such as Oktoberfest and the Savannah Film Festival.

Because Savannah is known for its genteel gardens, squares and mansions, plan to spend a fair share of time outside. A good bet is to explore the city via a Savannah Tour of Homes and Gardens walking tour, which takes visitors through many of the city's gorgeous historic homes. Set the creepy mood on a Blue Orb Tours walking ghost tour. Or get close to the dead with a visit to the Bonaventure Cemetery, the setting for the famed book, Midnight in the Garden of Good and Evil. The moss-covered graves are the final resting places of Confederate soldiers, generals, plantation owners and scions of wealthy families.

Nashville, Tenn.

Nashville, Tennessee

Nashville, Tennessee

Photo by: Will Cameron

Will Cameron

Nashville takes its music very seriously — hey, it didn't earn the nickname "Music City" for nothin' — and fall amps up the sounds of the city with a full array of music festivals. Grab your cowboy hat and boots, and kick up your heels at the season’s best events: the Americana Music Festival and the biggest party in town, the CMA Awards.

Once you've gotten your music fill, wrap your head around Nashville's awesome autumn-themed offerings, such as ghost tours, haunted houses, corn mazes and scarecrow exhibits. The Nashville area is home to a fair share of spook-tacular hauntings, such as the abusive Bell Witch, the Body Farm and even a few alleged spirits at the Grand Ole Opry House, where apparently not all former country stars go gently into that good night.

New Orleans

New Orleans

New Orleans

Photo by: Getty Images

Getty Images

New Orleans' intrigue snaps into high gear come fall, as heat and humidity drop and the city's ghoulish past rises to the forefront thanks to spooky tours and events. Plan your visit around Halloween and be sure to attend the Voodoo Music Experience, a three-day festival of music, underground arts and culture and unusual crafts. Family-friendly Halloween-themed events include Boo at the Zoo, featuring games, a haunted house, a ghost train and trick-or-treating; Crawloween at the Insectarium, and Museum Mash at the Louisiana Children's Museum. Other memorable events include the Vampire Ball and Ghostly Galavant walking tour. Of course, for less kid-friendly fun, grab your sassiest costume and head to Bourbon Street to celebrate in creeptastic style.

Still, NoLa's spooky side isn't the only autumn draw to this incredible city. Festivals fill the calendar in October, including Crescent City Blues and BBQ, free, weekly Wednesday concerts in Lafayette Square and the New Orleans Film Festival. Finally, for the sports-minded traveler, check out a New Orleans Saints game at the famed Superdome; 'tis the season.

San Diego

San Diego Zoo Safari Park

San Diego Zoo Safari Park

Photo by: San Diego Zoo Safari Park

San Diego Zoo Safari Park

The gods of weather have graced San Diego with the perfect climate: comfortably warm, dry and typically sunny without ever being unbearably scorching. Autumn is no different in this city by the sea, but what does change is the departure of the summer crowds, leaving San Diego and its attractions quieter and more convenient to visit. Visitors might be tempted to forget that seasons have changed; it's still possible to snorkel in La Jolla Cove, surf at Mission Bay Park and take a hike at Palomar Mountain State Park well into October. Families should take advantage of October's free admission for kids three to 11 at the unparalleled San Diego Zoo, which also allows guests to camp overnight at the zoo through November by signing up for the Roar and Snore Safari program.

Autumn festivals include the Old Town San Diego Art Festival, La Jolla Art and Wine Festival and the Thanksgiving Dixieland Jazz Festival. To get into the Halloween spirit, head to the Haunted Trail of Terror in Balboa Park, when the urban park is transformed into a maze-like spookfest filled with frightful ghouls and spirits.

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