magazine | Travel | Destination Guides

12 Experiences You Will Want to Add to Your Fall Agenda

photo: Lauren Fair
Whether you staycation or vacation this fall, there’s a ton to do, see and eat. The bounty of the season is palpable as you drive along winding roads filled with colorful Aspen trees in Colorado, through the rolling vineyards of Sonoma’s wine country, or visit the apple orchards of upstate New York. If you’re looking for something to do to celebrate the season, try your hand at fall flower arranging in Charlottesville, check into Teton Village for a pampering session, explore the Hudson Valley’s cute towns and shops, or head to a food and wine festival in Guadalupe. Here, we’re diving into our fall agenda favorites.

Reporter: Alyssa Brown
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Host a Private Wine Tasting Party at Oyster Ridge learn more

Treat your nearest and dearest to a private wine tasting at Oyster Ridge and you’ll be in everyone’s good graces for the entire fall season. With sweeping views of the vineyards and hills of Santa Margarita Ranch, this gem of a property is an awesome place to let a long Sunday afternoon simmer.
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Photo: Lauren Fair
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Explore the Hudson Valley and stay at Cedar Lakes Estate learn more

With great apple orchards, vineyards, towns, shops and plenty of hiking trails, the Hudson Valley is an easy escape from the NYC grind, just in time for fall. Book in for a stay at Cedar Lakes Estate to have a premium spot for exploring the gems of the region.
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Attend a Fall Plants Workshop at Pharsalia Events learn more

This stunning Virginia flower farm has events throughout the fall that sound perfect for the at-home florist, gardener or landscape lover. Sign up for the October 4th class in wreath-making using dried flora, or the October 10th workshop where you’ll arrange fall flowers and blooms. Both events include a lovely catered lunch too.
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Photo: Canoe Bay
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Take a Romantic Getaway to Canoe Bay

Chetek, Wisconsin
Grab your boo and pack your bags for a weekend getaway to Canoe Bay, where you’ll spend your days exploring the colorful fall foliage. This luxury getaway offers cozy accommodations and wonderful farm-to-table dining right on the edge of the water. Check out their fall specials to score discounts on bookings.
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Go on a Wellness Mountain Getaway at Skylonda Lodge learn more

Set in the redwood forests of Woodside, this wellness retreat encourages guests to expand their yoga practice, hike and explore the area, and attend fitness classes, all while eating wholesome, nutritious meals. Skylonda Lodge offers 4-day retreats that are sure to help you reset for whatever the new season may bring.
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Photo: The Warfield
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Attend a Fall Show at The Warfield learn more

The fall lineup at The Warfield includes some of the absolute hottest singers and songwriters right now so make sure to add a show to your to-do list. Planning a holiday party for work or just for fun? You can rent out the space for grand, private parties.
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Photo: Life & Food
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Go to the Valle de Guadalupe Food & Wine Festival

Valle de Guadalupe, Baja, Mexico
When 30+ chefs get together with nearly as many wineries in Valle de Guadalupe, you’ve got yourself a reason to get out and dine and dance under the stars. This fabulous food and wine festival takes place on October 6th and brings together big local names with non-locals alike, to celebrate food, wine, music, artisans and all the things that make life so enjoyable. If you can’t make it to the region in time for the festival, check out one of Club Tengo Hambre’s Valle de Guadalupe Food + Wine Daycations next time you’re in town, they’ve got a solid lineup for fall.
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Pamper Yourself Before the Winter Crowds at the Caldera House learn more

Head out to Teton Village for a chill pre-season hang and soak up the healing energy of this beautiful region from the comfort of a super luxurious stay. Caldera House has just 8 suites and makes a fabulous hangout spot if you’re traveling with a couple of close friends and looking to be totally pampered.
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Photo: Tyler Nix
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Visit the Kona Coffee Cultural Festival

Kona, Hawaii
Hawaii’s oldest festival celebrates coffee, food, art, music, dance and all things local. The Kona Coffee Cultural Festival kicks off November 9th and runs through the 18th, which is right about the time you’ll be looking to escape the chill and head to the islands.
Photo: Sylvia Gil
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Host a Backyard Fall Dinner

Every host knows there’s no time of year better for hosting a dinner party than fall. With the bounty of the season, you can decorate your table in beautiful tones of ochre, peach, crimson and more while serving a delicious farmer’s market meal.
Photo: Drifters Wife
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Dine at Drifters Wife and Explore the Food Scene in Portland

Portland, Maine
Portland, Maine is a happening little hub of food connoisseurs, and newcomer Drifters Wife is already a big part of the scene. Pouring the best local biodynamic and organic wines, and creating daily menus that celebrate the best produce available, this spot seems to do everything with a thoughtful ease. Enjoy the autumnal bounty here and pop around town to sip seasonal brews.
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Tour & Taste at James E Pepper Distillery

Lexington, Kentucky
Lexington’s bourbon distilleries and tasting rooms are best hit up during the fall season, so you can bounce from one to the next (with a driver, of course) while soaking up the autumnal foliage and perfect weather. Be sure to book into James E Pepper for a tour of the historic distillery and a tasting.

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Happy favoriting!