Where to Travel this Fall

By Kelley Boymer
4 Oct 2023

photography by craig mackay

Fall is in the air and it’s the perfect time of year to hit the road and see the sights. As the leaves start to change into colorful vibrant shades and the weather gets cooler it makes for a great time to adventure. Fall is a season to wear your coziest sweaters, hike, explore, shop, take scenic drives and eat comforting seasonal foods. Head to some of our favorite places in New England and beyond this fall to experience the season to the max!

Looking for a fun destination to explore this fall? Today we are sharing some fun ideas for where to travel this season and enjoy all that fall has to offer.

Where to Travel This Fall

Woodstock, Vermont

We always like to start out with our hometown because although we may be biased, it is truly the best fall. It’s no secret, that foliage in Vermont is absolutely breathtaking and paired with the charming town of Woodstock, it just can’t be beat.

Head to Woodstock this fall and enjoy all your favorite fall delights from pumpkin spice lattes, pumpkin ice cream, hiking, apple picking, harvest celebrations and so much more! Check out our Woodstock, VT Fall Bucket List, 2-Day Itinerary, and Best Places to Eat, for all of our recommendations to explore while in town.

woodstock covered bridge

Charleston, South Carolina

Although Charleston isn’t a fall foliage destination per se, as an “evergreen city” the weather alone in fall makes it a beautiful time to visit. As temps cool down after the hot southern summer, Charleston comes to life with ghost tours, historic walking tours and all the southern comfort foods you could imagine. Head to one of the many rooftop bars for a drink or perhaps a cozy wine bar.

Visit the Edmonton-Alston House and browse the beautiful art collection at the Gibbes Museum. In September, Charleston Restaurant Week is a great opportunity to partake in special menus and excellent prices. MOJA Art Festival is another fall event in Charleston and many private homes open for public House and Garden Tours.

Grace Atwood has an excellent Charleston Guide as well.

Jess Ann Kirby visits Rainbow Roe in Charleston South Carolina

Kancamagus Highway, New Hampshire

Known for having some of the best fall foliage scenic views around, the Kancamagus Highway is a 35 mile stretch through the White Mountains. Drive the scenic roads or take your time and camp at one of the many campgrounds along the highway. If you’re looking to stay nearby check out North Conway.

Take the scenic drive on Highway 112 from North Conway to Lincoln. For an easy but stunning walk head to Echo Lake State Park. If you’re looking for more of a hike check out Cathedral Ledge (this is also a popular rock climbing spot). There’s incredible views from the top of North Conway and the White Mountains. Grab breakfast at Polly’s Pancake Parlor (this is actually in Sugar Hill). If you worked up an appetite hiking, check out Barley & Salt. Peak foliage is typically early-mid October.

Newport, Rhode Island

As a Newport native, Jess knows firsthand how magical Newport is in the fall. Summers in Newport can be overly busy and crowded and take away from the beauty of the island. As the crisp air of fall arrives, Newport begins to slow down a bit and this makes for a relaxing, peaceful vacation. Get your ocean fix with some fall foliage mixed in. Enjoy the cliff walk without the heat and humidity of summer. Explore the mansions, shop and dine in cozy bars and pubs.

Check out the Point neighborhood to see charming colonials decorated for fall. Stunning foliage is on display all around the island, walk down Bellevue Ave or take a cruise along Ocean Drive. Pick your own at Sweet Berry Farm and Rocky Brook Orchard. Trinity Church in town has an annual pumpkin patch, check their website for dates. Nitro has some yummy seasonal coffee drinks and bites.

Mad River Valley, Vermont

Jess and her family did a 48 hour trip to the Mad River Valley in Vermont and had a blast. The foliage was beautiful, the restaurants were delicious and the scenery was breathtaking. It’s also a very convenient and stunning drive from Woodstock (about 1 hour and 10 minutes). I know Jess is going to be sharing more about her trip this week, but definitely add it to your list for this fall. Check out the new hotel Madbush Falls in Waitsfield. Jess said their dinner was incredible!

Mad river valley

Acadia National Park, Maine

Acadia National Park is another place that welcomes the off season of fall with a wonderful sense of calm and beauty. If crowds aren’t your thing, experience the magic of Acadia National Park in the fall with cooler temps and the peace and quiet of the season. The perfect season for hiking, biking and adventuring amongst the gorgeous foliage. Check out the Night Sky Festival if you are visiting in late September. Head to Bar Harbor to stroll the streets, browse in shops and enjoy a warm bowl of creamy chowder in cozy pubs and bars.

New York City

There is something magical about New York City in the fall. Maybe it’s a nostalgia created by movies growing up, but the image of a cool, crisp walk through Central Park just feels so romantic and cozy. Head to the big apple to enjoy your fall getaway in the city. Get your taste of fall foliage in the park and enjoy walking the streets– shopping, eating and seeing shows. Check out seasonal events like the Great Jack O’Lantern Blaze, Lightscape at Brooklyn Botanic Garden, Pumpkin Nights at the Bronx Zoo, Fall-O-Ween at the New York Botanical Gardens, The Great Gatsby Party, and The Secret World of Elephants exhibit at the American Museum of Natural History.

Photo by Sarah Brown on Unsplash

Lenox, Massachusetts

The Berkshires are a popular destination for urbanites during the fall due to the natural beauty and gorgeous fall hues. If a spa day is what you’re after, head to Canyon Ranch Lenox for a luxurious escape. Or try Kripalu Yoga Center for all your yoga and meditation needs. Lenox is a hot spot for delicious food, shopping, art, culture, hiking and biking. Explore this beautiful town and the mountains that surround it.

What’s your favorite fall destination? Let us know in the comments below!

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3 Comments

  1. Jane wrote:

    Alaska has some great nature, so make sure to pay a visit if you can 😀 And if you don’t like cold – Texas is pretty good(esp Big Bend NP, was there for the first time last year thanks to recommendation from folks at Gritr Sports ).

    11.7.23 | Reply
  2. messi wrote:

    Travel is the ultimate storyteller – every place has a tale to tell, and each traveler becomes a narrator in the grand epic of global adventures.Holiday Portugal The beauty of travel is not just in the breathtaking landscapes but also in the connections made with fellow wanderers, creating a global tapestry of friendships

    1.12.24 | Reply
  3. tessi wrote:

    Alaska has some great nature, so make sure to pay a visit if you can 😀 And if you don’t like cold – Texas is pretty good(esp Big Bend NP, was there for the first time last year thanks to recommendation from folks at Holiday Turkey

    1.12.24 | Reply

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