8 Great Autumn Getaways
Want to plan an easy fall trip? Here are some of our top picks for soaking up the season.
Hello readers!
Now that Labor Day is in the rear view, we’re here with a few ideas for a fall escape. This is one of our favorite seasons to travel — September and October still offer warm days but crowds are smaller (and prices are lower) than during peak summer. We’ll be heading out East ourselves soon and are looking forward to soaking up some early fall weather while still getting in a lobster roll or two by the water. Whether you’re seeking a relaxing week off or a quick getaway before holiday travel comes around, these spots fit the bill.
Of course, you could also plan a fall visit to San Francisco, the city we cover in our latest Field Guide. The guide includes a three-day itinerary with 30+ places to eat and drink, including our top bakeries, cocktail bars, dinner spots, and more. Learn how to download that below!
And before we log off for the weekend, we’ve got a couple things to add to your Weekend Reading list including a Midwest Living guide to supper clubs, a Garden & Gun dispatch from Montezuma, Georgia, and a Unicorn Review piece on the success of Michter's Distillery.
Thanks for being here!
— Amy Cavanaugh & Kenney Marlatt
8 Great Fall Getaways
From summer hot spots that slow down in the autumn to cities that come alive when the leaves start to fall, our picks below make for wonderful trips this season.
Portland, Maine
Most people flock to Maine’s capital city during the summer, but fall is the best time to go, especially if you’re planning a food-filled trip. Restaurants that have hours-long waits in August (hello, Eventide!), are chill enough during the fall season so you can walk right in for freshly shucked oysters and bowls of chowder. The crisp air lends itself to strolls around town, so start your morning with a maple latte at Bard Coffee before making your way to Bread & Friends for thick slices of French toast with crème fraîche. From there, you could spend the day at the Portland Museum of Art or go shopping (we love Browne Trading Co. for tinned seafood and other goodies).
Get more Portland picks: Field Guide + Weekend Getaway newsletter
McMinnville, Oregon
Wine tasting is a lovely autumn activity, particularly since harvest season in Oregon’s Willamette Valley takes place during September and October. Make the town of McMinnville, located an hour’s drive from Portland, your home base for visiting wineries like Brittan Vineyards, Soter Vineyards, and Day Wines. McMinnville is a walkable town with a street of nice shops, like Third Street Books, and plenty of great restaurants. You can grab breakfast pastries at Alchemist’s Jam, pick up chorizo tacos at Tacos El Gordo, and settle in for a cozy dinner at Thistle.
Get more McMinnville picks: Field Guide + Weekend Getaway newsletter
Burlington and Stowe, Vermont
Vermont is one of the states that does fall best — the foliage is top-notch, the towns are cute and cozy, and they do maple products better than anywhere else. The nearby towns of Burlington, which is Vermont’s largest city and home to the University of Vermont, and the ski town of Stowe make for a great fall getaway. You can take rambles in the woods or along Lake Champlain and then indulge in seasonal delights like hoppy beers, Montreal-style bagels, and pizza topped with local produce.
Get more Burlington and Stowe picks: Overnight Stay newsletter
Paducah, Kentucky
Located along the Ohio and Tennessee Rivers, the artsy town of Paducah makes for a great fall weekend. Visit the National Quilt Museum and the Paducah School of Art & Design, then spend time strolling the downtown area, which has shops and lots of good places to eat and drink. Sara Bradley’s restaurant Freight House serves plates just right for the season (we love the shrimp and grits with spicy pork shank, button mushrooms, and New Orleans barbecue sauce over tangy pimento cheese grits). Add in apple cider or pumpkin spice doughnuts and a fun bourbon bar, and you have an ideal autumn weekend.
Get more Paducah picks: Overnight Stay newsletter
Hudson, New York
Many New Yorkers likely know the vast delights that await in the bucolic Hudson Valley. From beer and cider makers to farms that provide restaurants and markets with local produce, there’s a lot of tasty stuff happening here. If you stay in downtown Hudson, you’ll be right in the middle of shopping and restaurants, and a stone’s throw from other towns, like Kingston. Make a picnic of snacks from Talbott & Arding Cheese and Provisions, go for a hike, and then come back to town for a cozy dinner at Rivertown Lodge.
Get more Hudson picks: Field Guide + Weekend Getaway newsletter
Charlottesville, Virginia
College towns come alive in the fall, when the students return, football games are in season, and it feels like everyone has turned a page. One of our favorite college towns is Charlottesville, home to the University of Virginia. Wander the beautiful campus or shops on the downtown mall, then pick up ham biscuits at Stock Provisions and a spiced honey cardamom latte at Lone Light Coffee. You can also explore the many wineries in the area or drive along the Blue Ridge Parkway to take in the foliage. For dinner, you’ll want to book The Alley Light, which was a 2024 Landmark List inductee.
Get more Charlottesville picks: Field Guide + Weekend Getaway newsletter
Viroqua, Wisconsin
If you like cozy cabins, quaint towns, and locally sourced food, head to Viroqua, where there is just enough great stuff for a delicious long weekend. A town of 4,500 people, Viroqua is located in Wisconsin’s Driftless Region, where the soil is just right for growing wonderful produce (there are 200 organic farms in the county), and you’ll find cheesemakers and other producers in the area. Start your day with maple lattes and scones at Wonderstate Coffee before you head out on a ramble or just tuck yourself up in your cabin to relax by the fire.
Get more Viroqua picks: Overnight Stay newsletter
Grand Rapids, Michigan
Grand Rapids is best known for its beer scene (we recommend the Belgian-style beers at Brewery Vivant or getting a pint of sour ale or a glass of natural wine at Speciation Artisan Ales), but there’s so much more happening here too, including bakeries and tropical bars. Roam the 158-acre Frederik Meijer Gardens & Sculpture Park by day to see the art amidst the colorful foliage, or hit some of the many hiking or biking trails in the area. When you get back, head to Butcher’s Union for a dinner of seasonally changing steak preparations, local veggies, and whiskey cocktails.
Get more Grand Rapids picks: Overnight Stay newsletter
Download All Our San Francisco Recommendations
We’ve compiled all our San Francisco favorites into a three-day guide with 30+ vetted recommendations. Our Field Guides — which are free for paid subscribers — include itineraries with picks for breakfast, lunch, dinner, and drinks. Each entry features links to Google Maps and Instagram. Our guides are designed for your phone and you can download them to read offline, making them an on-the-go reference for your trip. Paid subscribers can find the code to get the Field Guide to San Francisco — and any other Field Guide you’d like! — for free in this month’s Weekend Getaway newsletter. A paid subscription also includes our Google Map (which has 900+ vetted places across the country!) and our Substack chat, where you can ask us for travel advice.
THE MIDWEST
Dinner with a View at These Lakeside Supper Clubs: “At Midwest supper clubs, you can step through the door and into another era where time slows, the lights stay low, and tradition comes with a side of horseradish,” writes friend of American Weekender Kelly Aiglon in Midwest Living. “These dinner spots aren’t just restaurants; they’re rituals. Think slow-roasted prime rib, crackling fireplaces, and cocktails strong enough to earn your respect. But what makes these seven institutions a cut above the rest? They all come with a waterfront view.” A good list here that includes some of our Wisconsin favorites like Ishnala Supper Club in Lake Delton and the Hobnob in Racine. (Midwest Living)
GEORGIA
Biscuits, Burgers, and Dedication Keep a Small-Town Georgia Institution Humming: John T. Edge has a dispatch from Montezuma, Georgia, where he visits a small-town diner called Troy’s Snack Shack. “Little has changed in seven decades of operations,” writes Edge. “Troy’s is still short on comforts: No heater runs in the winter, no AC pumps Freon in the summer. And the food — cooked to order from honest, never-frozen ingredients — is still straight-up delicious. Baked by Angie, the biscuits are throwback three-ingredient beauties. Drumsticks and thighs, cut from small chickens instead of poultry plant behemoths, come robed in a salty crust that shatters when you bite. Chili slaw burgers, beautifully sloppy and about the size of a deck of cards, cost less than a single from McDonald’s.” You had me at the biscuits. (Garden & Gun)
KENTUCKY
The Slow Burn Success of Michter’s: The Unicorn Review recently talked with Michter's Distillery President and American Weekender reader Joseph Magliocco about his journey turning a defunct label into one of America’s top whiskey brands. “Nowadays, it’s hard to find a whiskey drinker who doesn’t enjoy Michter’s,” writes Susannah Skiver Barton. “The brand is the only one to be named “World’s Most Admired Whisky” by Drinks International twice. But it’s taken Magliocco and his company nearly 30 years to get to this point, and the journey wasn’t always smooth or straightforward.” Who’s ready for an Old Fashioned? (The Unicorn Review)
— Compiled by Kenney Marlatt
Want more? Chat with us on Substack, download our Field Guides, check out our archives, or follow us on Instagram @americanweekender. We’ll be back on Friday.
Heading to Portland tomorrow!! Thanks for the recs!
Charlottesville is definitely a great trip! Found some amazing books there.