I have my windows open and fresh air blowing through the house, and for the first time this year, I can officially say it smells like fall. This is my favorite time of year, and as someone who's pretty frugal, it's also one of my favorite times to travel.
Shoulder season can be a sweet spot for a long weekend away. Summer crowds have started to thin, the holiday travel rush hasn't arrived and the season brings changing leaves, cooler temperatures, seasonal food and festivals worth planning a trip around. I often find good travel deals this time of year, too. And you don't need a week off to squeeze in one more memorable trip before the holidays.
If you're ready to celebrate the start of fall with one more adventure, I've found five destinations with plenty happening from late September through early November.
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Enjoy a warmer fall weekend in Nashville, Tennessee
If you're not quite ready to trade your light jacket for a winter coat, head south to Nashville. Fall brings cooler temperatures to Music City, but there's still plenty of opportunity to spend time outside. Better yet, Nashville's fall calendar gives you plenty of flexibility when choosing a weekend.
There's plenty to fill a long weekend beyond Nashville's famous music scene. The free Tennessee State Museum sits next to Bicentennial Capitol Mall State Park and the Nashville Farmers' Market, making it easy to visit all three in one outing.
Head to Centennial Park to see Nashville's full-scale replica of the Parthenon, then grab hot chicken at Red's 615 Kitchen or stop by nearby Springwater, one of the city's oldest dive bars. For a taste of old-school Nashville, venture west to the iconic Loveless Cafe or make your way to Monell's for its family-style Southern cooking.
Fall events to consider
- Nashville Oktoberfest, Oct. 1 - 4: Enjoy German food, live music, beer, vendors and other festivities during Nashville's annual Oktoberfest.
- Cheekwood Harvest, through Nov. 1: Celebrate fall among more than 100,000 pumpkins, seasonal gardens, live music and other activities at Cheekwood Estate & Gardens.
- Grand Ole Opry's 100th birthday celebration, select dates in October: The Opry's centennial celebration continues with performances throughout the month.
Where to stay
The Printing House Hotel by Hilton in downtown Nashville is a newer boutique hotel inspired by Nashville's history as a printing and publishing hub. Its design nods to that heritage, while the fifth-floor Letterpress Lounge & Terrace offers cocktails, small bites and live music.
For a more traditional stay, Hilton Garden Inn Nashville is less than three blocks from the Country Music Hall of Fame and Bridgestone Arena and has a rooftop pool with city views, plus on-site restaurants and bars.
Walk through history in Boston and Salem, Massachusetts
You don't have to choose between a Boston getaway and a spooky weekend in Salem. The two Massachusetts cities are close enough to combine into one fall trip, with the MBTA commuter rail connecting Boston's North Station and Salem in about 30 minutes.
In Salem, history extends well beyond the infamous witch trials of 1692. Tour The House of the Seven Gables, explore the collections at the Peabody Essex Museum or hop aboard the Salem Trolley for a narrated tour covering the city's witch trial, literary and maritime history.
October is Salem's busiest month, so expect crowds, particularly as Halloween approaches. The city encourages visitors to use public transportation during the busiest weekends rather than drive.
Back in Boston, continue your walk through history along the Freedom Trail, or explore Beacon Hill and the city's historic neighborhoods. If you want to add a little spooky history to the weekend, October also brings seasonal tours and events around Boston.
Fall events to consider
- Salem Haunted Happenings, throughout October: Salem's month-long Halloween celebration includes parades, markets, performances, tours and special events throughout the city.
- Salem Night Faire, Oct. 16 - 17 and Oct. 23 - 24: Head to Pioneer Village after dark for vendors, performances, ghost stories, food and hot cider.
- Wicked, through Nov. 15: Lean into the weekend's witchy theme with a performance of Wicked at Boston's Citizens Opera House.
- Freedom Trail Lantern Tour, select dates beginning Sept. 24: Explore the darker side of Boston's Revolutionary history on an evening lantern-lit tour along the Freedom Trail.
- Boston Lights, through Nov. 8: Walk among colorful lantern displays and illuminated scenes during the annual nighttime experience at Franklin Park Zoo.
Where to stay:
If Salem is the focus of your weekend, Hampton Inn Boston Peabody is about five miles from Salem and seven miles from The House of the Seven Gables.
If you'd rather make Boston your home base, Hilton Garden Inn Boston Logan Airport is less than five miles from the airport and downtown Boston, with a free shuttle that also takes guests to the Wood Island MBTA station.
Eat, listen and explore your way through New Orleans
Fall is a great time to experience New Orleans without waiting for Mardi Gras. The city's October and early November calendar is packed with food festivals, live music and cultural events, but you don't need a festival to fill a long weekend here.
Start with a beignet and iced coffee at Cafe Du Monde. The French Quarter location is iconic and admittedly touristy, but sitting outside with a beignet while music drifts through the Quarter is part of the fun. For a quieter experience, I prefer the City Park location. From there, art lovers can visit the New Orleans Museum of Art and the Sydney and Walda Besthoff Sculpture Garden, which offers free guided tours on Sundays.
Another favorite is The Historic New Orleans Collection, a free museum in the French Quarter with rotating exhibitions exploring the city's history and culture. Or hop aboard the St. Charles streetcar and ride through the Garden District and Uptown. If you'd rather trade the city for nature for a few hours, consider a swamp tour for a chance to see Louisiana's incredible wetlands and wildlife.
Fall events to consider
- National Fried Chicken Festival, Oct. 2 - 4: Sample fried chicken from restaurants around the country while enjoying live music and other festivities along the New Orleans lakefront.
- Crescent City Blues & BBQ Festival, Oct. 9 - 11: Combine two New Orleans specialties with a weekend of blues and barbecue in Lafayette Square.
- New Orleans Film Festival, Oct. 22 - 26: Catch screenings and events during one of the region's major annual film celebrations.
- Tremé Fall Festival, Oct. 24: Celebrate the historic Tremé neighborhood with music, food and local culture.
- Día de los Muertos Festival, Nov. 1: Celebrate Day of the Dead with music, art and cultural traditions.
Where to stay
For a hotel with some New Orleans history of its own, The Roosevelt New Orleans, a Waldorf Astoria Hotel, dates back more than a century. Its restoration preserved architectural details including mosaic tile, plasterwork and coffered ceilings, while the Sazerac Bar features elegant woodwork and Art Deco murals.
For a more casual downtown option, Hilton Garden Inn New Orleans French Quarter is two blocks from the French Quarter and has an 11th-floor lobby lounge and rooftop pool with stunning city views.
Step into American history in Williamsburg, Virginia
Fall is an especially fitting time to visit Virginia's Historic Triangle as the country celebrates its 250th anniversary. Williamsburg, Jamestown and Yorktown put centuries of American history within a relatively small area, while cooler temperatures make it easier to spend your days walking historic streets and exploring the outdoors.
Give Colonial Williamsburg plenty of time, particularly if you want to tour the historic buildings. Many house tours are guided and operate on different schedules, so trying to squeeze the entire historic area into a few hours can leave you watching the clock instead of enjoying it.
At Jamestown Settlement, explore the museum before heading to nearby Historic Jamestowne to see the archaeological site where researchers continue to uncover the story of the original settlement. When you're ready for a change of pace, walk or bike a portion of the Virginia Capital Trail, explore Freedom Park or head to York River State Park. For dinner away from the main Colonial Williamsburg walking area, I have a soft spot for Second Street American Bistro.
Fall events to consider
- Yorktown Art Stroll, Sept. 27: Browse paintings, photography, pottery, jewelry and other work from regional artists along the Yorktown waterfront.
- An Occasion for the Arts, Oct. 3 - 4: See work from more than 150 juried and local artists alongside live entertainment, food and other activities in Williamsburg.
- Yorktown Wine & Oyster Festival, Oct. 3 - 4: Sample Virginia wines and oysters while enjoying live music along the Yorktown waterfront.
- Yorktoberfest, Oct. 25: Spend an afternoon sampling craft beer and cider with food, vendors and live music in Yorktown.
Where to stay:
The Hampton Inn & Suites Williamsburg Historic District is just a half-mile from Colonial Williamsburg, making it a convenient home base for a history-focused weekend. Parking, hot breakfast and WiFi are included, and there's an indoor pool. Hampton Inn & Suites Williamsburg-Central is another option about five minutes from Colonial Williamsburg, with free breakfast and parking plus indoor and outdoor pools.
Get a taste of Bavaria in Leavenworth, Washington
You don't have to cross the Atlantic to get a taste of Bavaria this fall. Leavenworth sits against the Cascade Mountains and leans heavily into its Bavarian theme, with alpine-style buildings, German restaurants and shops filling its compact downtown.
Add fall foliage and cooler mountain weather, and this may be one of the most picturesque long-weekend trips on the list.
Spend some time wandering downtown, but leave room to explore beyond the shops. Walk the trails along the Wenatchee River at Waterfront Park, visit the Greater Leavenworth Museum or stop at one of the area's wineries and tasting rooms. And if you're coming for Oktoberfest, this is the weekend to embrace the theme and order the bratwurst.
Fall events to consider
- Washington State Autumn Leaf Festival, Sept. 25 - 27: Celebrate the arrival of fall with a weekend of activities and the festival's Grand Parade through downtown Leavenworth.
- Leavenworth Community Farmers Market and Village Art in the Park, Sept. 26: Add local produce, handmade goods and art to an Autumn Leaf Festival weekend.
- Leavenworth Oktoberfest, Oct. 2 - 3, 9 - 10 and 16 - 17: Celebrate over three weekends with live entertainment, German food, beer and Bavarian-inspired festivities throughout town.
Where to stay:
Hampton Inn & Suites Leavenworth is about a mile from the restaurants and shops downtown, as well as the riverside trails at Waterfront Park. Hot breakfast and parking are included, and there's an indoor pool.
If you'd rather stay outside the bustle of Leavenworth during a busy festival weekend, Hilton Garden Inn Wenatchee is about 22 miles away on the banks of the Columbia River. It's less than a mile from downtown Wenatchee and near Pybus Public Market, with an on-site restaurant, patio and indoor pool.
Make your fall getaway go further
If you're staying at a Hilton property, joining Hilton Honors before you book can unlock additional benefits. Members can access exclusive rates and earn Points on eligible stays booked directly with Hilton.
Booking directly also comes with Hilton's Price Match Guarantee, while Gold and Diamond members may qualify for space-available room upgrades at select properties. The Hilton Honors app offers Digital Check-in, room selection and Digital Key at participating hotels, which can help streamline a short getaway.
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