Trip ideas · 9 cities ranked
Fall Getaways for Couples: 9 Grown-Up Cities for Autumn
Autumn is the grown-up season for travel: the summer crowds thin out, the evenings are cool enough for a rooftop and the dining rooms are easier to book. These are the nine cities we'd pick for a fall trip for two, with the seasonal dates that matter.
Some links on this page go to booking partners. If we join their affiliate programmes we may earn a commission when you book, at no extra cost to you. It never decides what we recommend. How we make money.
Seasonal dates below come from our September 2026 checks of each city. Some places close for the winter in mid- to late October, so the order roughly runs from early autumn to late.
How we ranked them
- Autumn is a good time to go: our city research names autumn (or its start) as a good season.
- Something at its best in fall: colour, crisp weather, a season that's still running or one that's just opened.
- Checked dates: closures and season ends are flagged, so you don't plan around something that's shut.
- Couples' evenings: a rooftop, a view or live music within easy reach of dinner.
At a glance
| # | City | Best for | Autumn timing | Ideal stay |
|---|---|---|---|---|
| 1 | Asheville | Mountain colour | October for the colour; book early | 2 to 3 nights |
| 2 | Portland | Crisp coastal weekends | Late September to mid-October | 2 to 3 nights |
| 3 | Chicago | City culture in cool weather | River cruise runs to November 22 | 3 to 4 nights |
| 4 | Santa Barbara | Mild weather and wine | Lotusland open to October 31 | 3 nights, 4 with a day in wine country |
| 5 | San Diego | Late-summer warmth | September to November | 3 to 4 nights |
| 6 | Scottsdale | The desert season opening | Season runs October to May | 3 nights, 4 with a Sedona day |
| 7 | Sedona | Red rock hikes and dark skies | Hiking weather returns | 3 nights, with a day in the Verde Valley |
| 8 | Nashville | Rooftops and songwriters | Best rooftop weather | 3 nights |
| 9 | Austin | Bats, blues and barbecue | Bats fly until early November | 3 nights |
1. Asheville, North Carolina
Best for: Mountain colour. Autumn timing: October for the colour; book early.
October is Asheville's colour month and its busiest, so book dinners and hotels well ahead. Drive up to Craggy Gardens for a 360-degree summit view (check Parkway road status first), tour Biltmore, and finish at the Grove Park Inn.
Craggy Gardens & Craggy Pinnacle
Blue Ridge Parkway, milepost 364, about 40 minutes north
Heads-up: Parkway repairs continue north of here; check the NPS road status page before you drive.
The easiest big view near Asheville: a 1.5-mile round trip through a rhododendron tunnel to a 360-degree summit. The visitor center and Craggy Pinnacle trail reopened in September 2025 after Helene repairs.
Biltmore Estate
Biltmore Village entrance, south of downtown
George Vanderbilt's French Renaissance chateau, with a self-guided audio tour of the house, formal gardens and a winery in Antler Hill Village where admission includes a free tasting (21+). Timed tickets; buying online is cheaper.
The Spa at The Omni Grove Park Inn
290 Macon Ave
A 43,000-square-foot underground spa of stone arches and tunnels, with waterfall pools, a lap pool under 6,500 fibre-optic stars, saunas and eucalyptus steam rooms.
Plan it
- A Weekend in Asheville for Grown-Ups
- 3 Days in Asheville: A Grown-Up Itinerary
- Things to Do in Asheville for Couples
- All of Asheville for grown-ups
Asheville hotels on Stay22Biltmore Estate tickets (Viator)LaZoom comedy bus tour (Viator)
Suggested base: Downtown, walkable to the restaurants and bars, or the Grove Park Inn for a resort stay. Fly into Asheville Regional (AVL).
2. Portland, Maine
Best for: Crisp coastal weekends. Autumn timing: Late September to mid-October.
Late September and early October are quieter and often the nicest weather. Go early: in 2026 the Portland Head Light museum and the Portland Observatory close after October 12, and the Lobster Shack at Two Lights after October 25. Eventide and Fore Street stay open.
Portland Head Light & Fort Williams Park
1000 Shore Rd, Cape Elizabeth (15 minutes)
Heads-up: The lighthouse museum closes for the season after Indigenous Peoples Day (October 12, 2026).
The classic Maine lighthouse, on the rocks inside a free public park with old gun batteries, the Goddard Mansion ruin and a small cove beach. The park is open sunrise to sunset year-round; parking is by card meter.
Eventide Oyster Co.
86 Middle St, Old Port
A James Beard Award-winning raw bar with fresh oysters and shellfish and the famous brown butter lobster roll. Indoor and outdoor seating.
Fore Street
288 Fore St
Portland's landmark since 1996: a big old warehouse room around a wood-fired oven, grill and turnspit, with a menu that changes daily with what farmers and fishermen bring in. Open nightly from 4:30 p.m.; reservations by phone.
Plan it
- A Weekend in Portland, Maine for Grown-Ups
- 3 Days in Portland, Maine: A Grown-Up Itinerary
- Things to Do in Portland, Maine for Couples
- All of Portland for grown-ups
Portland hotels on Stay22Old Port food tour (Viator)Lighthouse tour from Portland (Viator)
Suggested base: The Old Port, walkable to the restaurants, bars and ferry. Fly into Portland International Jetport (PWM).
3. Chicago, Illinois
Best for: City culture in cool weather. Autumn timing: River cruise runs to November 22.
The architecture river cruise runs until November 22 in 2026, and the best rooftops keep going into autumn with heaters, fire pits and glass rooms, like Cindy's over Millennium Park. Evenings belong to the Green Mill.
Chicago Architecture Center River Cruise
112 E. Wacker Dr (riverfront)
A 90-minute cruise aboard First Lady down all three branches of the river, with a docent covering 50-plus buildings and the bascule bridges. The single best introduction to the city. The 2026 season runs mid-March to late November.
Cindy's
Chicago Athletic Association, 12 S. Michigan Ave
A 13th-floor glass-atrium restaurant and terrace looking over Millennium Park and the lake. Fire pits in winter, open-air seats in summer.
The Green Mill
Broadway, Uptown
The legendary jazz lounge (Al Capone's booth is still there), with live music seven nights a week. Cash only, no reservations, and a serious listening room.
Plan it
- 2 Days in Chicago: A Weekend for Grown-Ups
- 3 Days in Chicago: A Grown-Up Itinerary
- Best Rooftop Bars in Chicago for Grown-Ups
- All of Chicago for grown-ups
Chicago hotels on Stay22Chicago Architecture Center River Cruise (GetYourGuide)
Suggested base: River North or the Loop near Michigan Avenue. Fly into O'Hare (ORD) or Midway (MDW).
4. Santa Barbara, California
Best for: Mild weather and wine. Autumn timing: Lotusland open to October 31.
Autumn is mild and less busy than summer. Book Lotusland before it closes for the season after October 31, taste your way around the Funk Zone's Urban Wine Trail, or take a day in Santa Ynez wine country with a driver.
Ganna Walska Lotusland
Montecito (address given on booking)
Heads-up: Open for the 2026 season until October 31; reopens February 17, 2027.
Ganna Walska's celebrated Montecito garden, seen on a two-hour self-guided or docent-led visit. Visits are Wednesday to Saturday at 9:30 a.m. or 1:30 p.m., by advance reservation only; book about three weeks ahead.
The Funk Zone and the Urban Wine Trail
Funk Zone, between State St and the beach
More than 20 tasting rooms pouring Santa Barbara County wines, most of them in the converted warehouses, murals and galleries of the Funk Zone, with a second cluster on Anacapa Street and El Paseo downtown.
Santa Ynez Valley wine country
About 45 minutes over the hill from Santa Barbara
Pinot noir and chardonnay from the Sta. Rita Hills, Rhône and Bordeaux grapes further inland, and small tasting-room towns such as Los Olivos and Solvang. A tour with a driver saves arguing over who drives.
Plan it
- A Weekend in Santa Barbara for Grown-Ups
- 3 Days in Santa Barbara: A Grown-Up Itinerary
- Things to Do in Santa Barbara for Couples
- All of Santa Barbara for grown-ups
Santa Barbara hotels on Stay22Funk Zone wine walk (Viator)Santa Ynez wine tour (Viator)
Suggested base: Downtown or the waterfront, walkable to State Street, the Funk Zone and the beach. Fly into Santa Barbara Airport (SBA).
5. San Diego, California
Best for: Late-summer warmth. Autumn timing: September to November.
September to November is lovely in San Diego: warm, with fewer crowds than summer. Watch the sun go down from Sunset Cliffs, then dinner at George's at the Cove or on the Hotel del Coronado patio.
Sunset Cliffs Natural Park
Sunset Cliffs Blvd, Point Loma
A mile and a half of sandstone cliffs, arches and caves on Point Loma's ocean side, and San Diego's favourite place to watch the sun go down (and look for the green flash).
George's at the Cove
1250 Prospect St, La Jolla
A La Jolla institution for more than 40 years, with three levels over the cove: the casual Ocean Terrace rooftop and the dressier dining room below, all facing the Pacific sunset.
Hotel del Coronado: Babcock & Story Bar and Sun Deck
1500 Orange Ave, Coronado
The 1888 beachfront hotel's restored mahogany bar opens onto a big patio facing the Pacific, with live music Thursday to Saturday from 6 to 10 p.m.; next door, the Sun Deck has fire pits for the sunset.
Plan it
- A Weekend in San Diego for Grown-Ups
- 3 Days in San Diego: A Grown-Up Itinerary
- Things to Do in San Diego for Couples
- All of San Diego for grown-ups
San Diego hotels on Stay22San Diego harbor dinner cruise (Viator)USS Midway Museum tickets (Viator)
Suggested base: Little Italy or the Gaslamp Quarter, or Coronado for the beach. Fly into San Diego International (SAN).
6. Scottsdale, Arizona
Best for: The desert season opening. Autumn timing: Season runs October to May.
Scottsdale's season starts in October, when the heat breaks and Camelback Mountain is hikeable again early in the day. Watch sunset from elements, and walk the Desert Botanical Garden in the evening light.
Camelback Mountain (Echo Canyon Trail)
Echo Canyon trailhead, Phoenix / Paradise Valley
The city's signature climb: 1.14 miles each way, steep and strenuous, open sunrise to sunset. Allow 1.5 to 3 hours; skip it in summer heat and go October to May, early.
elements at Sanctuary Camelback Mountain
Sanctuary resort, Paradise Valley
Chef Beau MacMillan's seasonal restaurant on the slope of Camelback Mountain, with a wall of windows and a deck over Paradise Valley. It is at its best at sunset.
Desert Botanical Garden
1201 N Galvin Pkwy, Papago Park
More than 50,000 desert plants on 55 cultivated acres, with five themed trails through cactus, agave and wildflowers. Most people spend two to three hours; the evening light is lovely.
Plan it
- 3 Days in Scottsdale: A Grown-Up Itinerary
- Things to Do in Scottsdale for Couples
- Day Trips from Scottsdale for Grown-Ups
- All of Scottsdale for grown-ups
Scottsdale hotels on Stay22Sedona day trip from Scottsdale (Viator)Phoenix hot air balloon ride (Viator)
Suggested base: Old Town Scottsdale, or a resort at the foot of Camelback Mountain. Fly into Phoenix Sky Harbor (PHX).
7. Sedona, Arizona
Best for: Red rock hikes and dark skies. Autumn timing: Hiking weather returns.
Autumn brings hiking weather back to the red rocks: climb Cathedral Rock early (take the free Sedona Shuttle when it runs), watch sunset from the Airport Mesa overlook, and join an astronomer for stargazing, which starts earlier as the nights draw in.
Cathedral Rock Trail
Back O' Beyond Rd, off SR 179
Heads-up: Trailhead parking is closed on days the shuttle runs. Check sedonashuttle.com for the schedule.
A short but steep scramble up the slickrock to the saddle of Sedona's most photographed formation. The free Sedona Shuttle serves the Cathedral Rock trailhead from a park-and-ride, and the trailhead lot is closed on shuttle days; a Red Rock Pass is needed to park at trailheads.
Airport Mesa Scenic Overlook
Airport Rd, Airport Mesa
Sedona's classic sunset view across the whole red rock skyline, from the lot the airport runs on top of the mesa. Parking is $3 for the day (keep the receipt); cards and cash accepted. The short Airport View and longer Airport Loop trails start here.
Evening Sky Tours stargazing
Village of Oak Creek (Big Park), south on SR 179
Heads-up: Start times change with the season.
A professional astronomer walks you through the constellations, then at least six objects through big telescopes: planets, star clusters, nebulae and galaxies. Tours run year-round; in September they start at 8:30 and 10 p.m., in October at 8 and 9:30 p.m., and from November at 7:30 and 9 p.m.
Plan it
- A Weekend in Sedona for Grown-Ups
- 3 Days in Sedona: A Grown-Up Itinerary
- Things to Do in Sedona for Couples
- All of Sedona for grown-ups
Sedona hotels on Stay22Broken Arrow jeep tour (Viator)Verde Valley wine tour (Viator)
Suggested base: Uptown or near Tlaquepaque on SR 179, a short drive from the restaurants and trailheads. Fly into Phoenix Sky Harbor (PHX), about two hours' drive.
8. Nashville, Tennessee
Best for: Rooftops and songwriters. Autumn timing: Best rooftop weather.
Spring and autumn evenings are Nashville's best rooftop weather: L.A. Jackson for sunset, Harriet's on the 19th floor (21+). Then hear songwriters in the round at the Bluebird Cafe (book online; it sells out fast).
L.A. Jackson
Thompson Nashville, the Gulch
A polished indoor-outdoor rooftop on the Thompson hotel with skyline views and a Southern-leaning drinks list. DJs on some weekends; sunset is the calmer time.
Harriet's Rooftop
1 Hotel Nashville, 710 Demonbreun St (19th floor)
An upscale rooftop lounge on the 19th floor of 1 Hotel Nashville, with bespoke cocktails, light bites and tableside service. Strictly 21 and over. Open from 4 p.m. on weekdays and 11 a.m. at weekends.
The Bluebird Cafe
Green Hills (about 20 minutes from downtown)
A tiny strip-mall room where songwriters sit in the round and play the hits they wrote for other people. Two shows a night; it is a hushed, listening crowd.
Plan it
- 2 Days in Nashville: A Weekend for Grown-Ups
- Best Rooftop Bars in Nashville (Away from the Broadway Crowds)
- Things to Do in Nashville for Couples
- All of Nashville for grown-ups
Nashville hotels on Stay22Ryman Auditorium self-guided tour (Viator)Jack Daniel's Distillery day trip from Nashville (Viator)
Suggested base: Downtown near the Ryman, or the Gulch. Fly into Nashville International (BNA).
9. Austin, Texas
Best for: Bats, blues and barbecue. Autumn timing: Bats fly until early November.
The Congress Avenue bats fly at sunset until roughly early November; watch from P6's rooftop. Austin City Limits in October makes everything busier and pricier, so book early or go either side of it. Jazz at the Elephant Room runs seven nights a week.
Congress Avenue Bridge bats
Congress Ave bridge over Lady Bird Lake
Around 1.5 million bats, the world's largest urban bat colony, stream out from under the bridge around sunset, roughly mid-March to early November. Free, and strangely magical.
P6 at The LINE
The LINE Austin, 111 E Cesar Chavez St
A sixth-floor rooftop over Lady Bird Lake with Mediterranean small plates and a front-row view of the Congress Avenue bridge, so you can watch the bats fly out at sunset in season.
Elephant Room
315 Congress Ave (basement)
An old-school basement jazz bar under the 19th-century Swift Building, with live jazz seven nights a week since 1991 and a small cover ($5 to $10).
Plan it
- A Weekend in Austin for Grown-Ups
- 3 Days in Austin: A Grown-Up Itinerary
- Things to Do in Austin for Couples
- All of Austin for grown-ups
Austin hotels on Stay22Fredericksburg wine tour from Austin (Viator)Austin bat-watching cruise (Viator)
Suggested base: Downtown near Congress Avenue, or South Congress. Fly into Austin-Bergstrom International (AUS).
Later in the autumn
- Miami comes into season from November, and Joe's Stone Crab reopens on October 15. See the Miami itinerary.
- Key West: September and October are quiet but it's hurricane season, and some places close for a break. December to May is the dry season. See Key West for grown-ups.
- Las Vegas: Red Rock Canyon's timed-entry reservations start on October 1. See Las Vegas day trips.
Everything here was checked in September 2026. Hours, seasons and reservation rules change, so confirm with each venue before you go.
Questions people ask
Where is the best fall getaway for couples in the US?
Asheville in October for the mountain colour, if you book early. For a coastal trip, Portland, Maine in late September or early October, before seasonal places close in mid-October.
What closes in the fall in Portland, Maine?
In 2026 the Portland Observatory and the Portland Head Light museum close after October 12 and the Lobster Shack at Two Lights after October 25. The park at Portland Head Light stays open year-round.
Is fall a good time to visit Scottsdale?
Yes. The season runs October to May. Summer days regularly pass 100°F and the city can close trails like Camelback in the middle of the day in excessive heat, so autumn is when hiking and patio evenings come back.
Which fall getaway is best for mild weather?
San Diego (September to November is warm with fewer crowds) and Santa Barbara (spring and autumn are mild and less busy than summer).