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Where To Go In October For Fun Fall Activities & Events

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October is an ideal month to plan a vacation: fall foliage is at its peak, the weather has found a comfortable midpoint between scorching summer highs and chilly winter lows, and autumn activities abound.

Where To Go In October For Fall Vacations

From the shores of Cape Cod to the mountains of New York, we’ve handpicked 10 fall getaways that are at their peak in October. Each brims with fun—apple picking or wine tasting, anyone?—guaranteeing a great day out at any of our top October vacation spots. Since it’d be impossible to mention all of the classic fall attractions in each city, we’ve highlighted our favorites to check off your fall bucket list.

Make your seasonal stay extra special by booking a vacation rental on FlipKey, and enjoy a comfortable place to relax after a day of merriment. Choose a log cabin and take in the colorful mountain landscape from your private hot tub, or rent a spacious vacation home so your family can spread out at the end of the day. With more than 300,000 rentals to choose from, you’re sure to find just what you’re looking for!

Accord, New York | Westwind Orchard & Cidery

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Located in the shadow of the Catskill Mountains, Westwind Orchard & Cidery is the place to be every weekend from Memorial Day through the end of October. Stroll down the rows of apple trees, filling your sack with handpicked fruit along the way. At the Cidery, sample traditional apple cider, cider with a raspberry twist, and more—all made from the fruits grown on site. And what could be more fall than a mug of sweet apple cider? A freshly baked doughnut dunked in cider!

View all rentals in Accord on FlipKey!

Kansas City, Kansas | Cider Hill Family Orchard

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Cider Hill Family Orchard is just one of the many fall attractions that make Kansas City a top spot for October getaways. Whether you’re in the mood for pumpkin and apple picking, pond fishing, or a relaxing hayride, this family-run orchard has it all. Pack a picnic lunch to enjoy under the shade of one of the big trees out back, or purchase yummy treats like cider doughnuts and kettle corn to enjoy in the comfort of your Kansas City vacation home. Your visit to the Cider Hill Family Orchard will undoubtedly be fun-filled.

View all rentals in Kansas City on FlipKey!

Richmond, Virginia | Richmond Folk Festival

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Mid-October, Richmond floods with folk music enthusiasts from around the country. The city’s eclectic festival features a mix of musicians, dancers, artists, and more, celebrating unique traditions from all over the world. Bounce from stage to stage swaying to the beat of the music, sample a variety of regional, ethnic, and traditional foods, or check out the cultural presentations—there’s no shortage of things to do here.

View all rentals in Richmond on FlipKey!

Guilford, Connecticut | Bishop’s Orchards

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“I will drive an hour to go to Bishop’s,” said one TripAdvisor traveler. We recommend saving yourself the long car ride though, and booking a rental in Guilford for an unforgettable fall getaway. From tasty fruit wine tastings and a gourmet market to the pick-your-own apple orchards and winding corn maze, there’s fun for all ages at Bishop’s Orchards. Here, you get to experience all of the classic fall activities your heart desires right in one place.

View all rentals in Guilford on FlipKey!

Grosse Pointe Park, Michigan | Core Orchards Detroit

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Surround yourself with nature just minutes from downtown Detroit at Core Orchards. It’s the first and only u-pick apple orchard in the area and a source of pride in the community. Designed to increase access to fresh, nutritious foods for those in the neighborhood, the orchard also serves as a welcoming fall attraction. Grab a bag of doughnuts to sweeten your tractor ride out to the farm where you can pluck mouthwatering honey-crisp apples straight from the branches. Once you visit Grosse Pointe Park, you’ll never wonder where to go in October again.

View all rentals near Grosse Pointe Park on FlipKey!

Steamboat Springs, Colorado | Strawberry Park Natural Hot Springs

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Take a break from crisp fall temperatures with a dip in the natural mineral springs at Strawberry Park. Located in Steamboat Springs, these balmy, 104-degree pools are particularly soothing after a day spent hiking through the foliage at Pike’s Peak. Unwind with watsu therapy in one of the private pools or enjoy a massage in the quiet of your own hut. These impressive hot springs are sure to make your autumn escape memorable.

View all rentals in Steamboat Springs on FlipKey!

Plymouth, Michigan | Plymouth Orchards & Cider Mill

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Apples and fall go hand in hand at Plymouth Orchards & Cider Mill in southeast Michigan. With several apple varieties ripe for the picking, award-winning, fresh-pressed cider, and family-friendly wagon rides, it’s the ultimate fall attraction packed into 60 acres of land. The best part though? Admission is free! Plan a trip to Plymouth this season to see for yourself why travelers describe Plymouth Orchards & Cider Mill as a “must visit in the fall!”

View all rentals in Plymouth on FlipKey!

Hampton Falls, New Hampshire | Applecrest Farm

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What’s fall without a weekend getaway in New England? Just 45 minutes north of Boston, the charming coastal town of Hampton Falls is where you’ll find Applecrest Farm, a picture-perfect place to indulge in all things autumn. With pick-your-own-fruit offerings, weekly fall festivals, and a farm-to-table dining experience, it’s no surprise that visitors describe it as a place with “something for everybody!” Plan your trip to this 4th generation gem, and stay just down the road at a spacious rental overlooking the ocean.

View all rentals near Hampton Falls rentals on FlipKey!

Flat Rock, North Carolina | Sky Top Orchard

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Does your ideal fall vacation involve colorful foliage, scenic mountain drives, picking apples and sipping on warm cider? In that case, we know just the place the travel to this October: Flat Rock, North Carolina. This quintessential fall vacation spot is home to Sky Top Orchard, a family favorite with lots of fun and memory-making in store for visitors. Pick a wagon-load of pumpkins, say hello to sheep, goats, chickens, and more in the barnyard, or simply take in the panoramic views. Book a vacation rental in Flat Rock and you’ll have your own u-pick orchard right in your backyard (well, almost!).

View all rentals in Flat Rock on FlipKey!

Wellfleet, Massachusetts | Wellfleet OysterFest

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Are you a foodie wondering where to go in October for a fall getaway? Consider Wellfleet, a quaint fishing town situated at the tip of Cape Cod. While many think of it as a summer destination, the annual Wellfleet OysterFest in October draws visitors to town from all over the region. The event celebrates Wellfleet’s eponymous shellfish grown in the cold, salty waters of Cape Cod Bay. From oyster shucking competitions and cooking demonstrations to spelling bees and live entertainment, there’s something for everyone at Wellfleet OysterFest.

View all Wellfleet rentals on FlipKey!

Best October Vacation Spots

  • Accord, New York
  • Kansas City, Kansas
  • Guilford, Connecticut
  • Grosse Pointe Park, Michigan
  • Steamboat Springs, Colorado
  • Plymouth, Michigan
  • Hampton Falls, New Hampshire
  • Flat Rock, North Carolina
  • Wellfleet, Massachusetts