Fall Travel Guide: 3 of the Best Fall Destinations in the USA
If you’re dreaming about crisp fall air, colorful leaves, apple cider donuts, pumpkins, cozy small towns, and maybe a little bit of spooky season, it’s time to plan a fall getaway.
Fall is one of the best times to travel in the United States, especially throughout the Northeast. You can experience incredible fall foliage, Halloween celebrations, historic towns, scenic road trips, seasonal festivals, and destinations that seem like they were MADE for this time of year.
Whether you’re looking for a Halloween weekend getaway, a romantic fall trip, a solo adventure, or a classic New England road trip, these three destinations deserve a spot on your fall travel list.
Here are three of the best places to visit in the USA this fall: Salem, Massachusetts; Sleepy Hollow, New York; and Vermont.
Before we get started, please note that this post may contain affiliate links, which means I may earn a commission if you make a purchase or booking through one of my links, at no additional cost to you. I only share products, services, and travel recommendations I genuinely believe may be helpful to my readers.
1. Salem, Massachusetts
Best for: Halloween, history + spooky season
If Halloween is your favorite holiday, Salem, Massachusetts, needs to be on your fall travel bucket list. I used to go to Salem every fall on a girls’ trip with my mother, sister, and best friends, and it was always such a great time!
Salem is famous for its connection to the Salem Witch Trials of 1692, but during the fall, the entire city transforms into one of the biggest Halloween destinations in the United States.
Throughout October, Salem hosts its annual Haunted Happenings, with special events, markets, performances, costumes, ghost tours, Halloween attractions, and festivities happening throughout the city.
Beyond Halloween, Salem is also filled with historic architecture, museums, waterfront views, restaurants, shops, and beautiful New England scenery.
5 Best Things to Do in Salem in the Fall
1. Learn about the Salem Witch Trials
Visit some of Salem’s historic sites and museums to learn more about the events of 1692. Popular stops include the Salem Witch Museum, The Witch House, and the Salem Witch Trials Memorial.
Viator Tour: Salem Witch Trials, Ghosts and History Walking Tour
2. Take a Salem walking or ghost tour
One of the best ways to experience Salem is on foot. Choose from historical walking tours, ghost tours, paranormal tours, witch-themed tours, and nighttime experiences throughout the city.
Viator Tour: History and Hauntings of Salem Guided Walking Tour
3. Visit The House of the Seven Gables
Explore the historic mansion that inspired Nathaniel Hawthorne’s famous novel, walk through the seaside gardens, and learn more about Salem’s maritime and literary history.
Viator Tour: Mysteries and Murders of Salem Guided Night-Time Walking Tour
4. Experience Salem Haunted Happenings
If you’re visiting during October, make time to experience some of Salem’s Haunted Happenings. The month-long celebration includes seasonal events, street performers, markets, attractions, food, costumes, and plenty of Halloween fun.
https://www.hauntedhappenings.org/
5. Find the Hocus Pocus filming locations
Fans of Hocus Pocus can visit several filming locations from the movie around Salem, including the famous Ropes Mansion and other recognizable spots throughout the area.
Viator Tour: The Official “Hocus Pocus” Movie Locations Tour of Salem
Where to Stay in Salem
Hawthorne Hotel
A historic Salem hotel located next to Salem Common and within walking distance of many of the city’s most popular attractions. It’s a great choice for travelers who want classic New England charm and a central location.
The Merchant
A stylish boutique hotel located inside a beautifully restored historic building in downtown Salem. The Merchant is ideal if you’re looking for a more intimate, elevated stay while still being close to Salem’s restaurants, shops, and attractions.
Salem Waterfront Hotel & Suites
Located near Pickering Wharf, this full-service hotel offers easy access to Salem’s waterfront, restaurants, shops, and historic attractions.
Salem Fall Travel Tip
Salem gets extremely busy as Halloween approaches, particularly on October weekends.
If you want the fall and Halloween atmosphere with slightly smaller crowds, consider visiting in late September or early October, and on weekdays rather than weekends.
Hotels, tours, restaurants, and popular attractions can also book well in advance, so this is one fall trip you don’t want to leave until the last minute.
Recommended trip length: 2–3 nights
2. Sleepy Hollow, New York
Best for: Spooky history, fall scenery + a weekend getaway
Yes, THAT Sleepy Hollow… the home of The Headless Horseman!
Located along the Hudson River in New York, Sleepy Hollow is forever connected to Washington Irving’s famous story, The Legend of Sleepy Hollow.
And during the fall?
The area fully embraces it.
You’ll find historic sites, cemetery tours, Halloween events, Headless Horseman references, thousands of glowing pumpkins, fall foliage, historic estates, and charming neighboring Tarrytown.
It’s one of the best fall weekend getaways from New York City and an especially fun destination for anyone who wants spooky season without the intensity of Salem in October.
I visited Sleepy Hollow on a solo trip a few years ago, and it was such a fun experience!
5 Best Things to Do in Sleepy Hollow in the Fall
1. Tour Sleepy Hollow Cemetery
Explore one of the area’s most famous historic sites and visit the final resting place of The Legend of Sleepy Hollowauthor Washington Irving. Seasonal daytime and evening tours are available.
https://visitsleepyhollow.com/events/sleepy-hollow-cemetery-tours
2. Experience The Great Jack O’Lantern Blaze
Thousands of hand-carved, illuminated pumpkins transform the landscape into an elaborate fall experience. The Great Jack O’Lantern Blaze is one of the Hudson Valley’s most popular fall attractions, so purchasing tickets in advance is highly recommended.
https://visitsleepyhollow.com/events/great-jack-olantern-blaze
3. Discover The Legend of Sleepy Hollow
Throughout the fall season, you’ll find performances, storytelling experiences, historic sites, and seasonal events celebrating Washington Irving’s famous tale and the Headless Horseman.
https://visitsleepyhollow.com/events/irvings-legend
4. Explore the area’s historic estates
Sleepy Hollow and the surrounding Hudson Valley are home to beautiful historic properties and estates. Combine the history with fall foliage and Hudson River views for a quintessential fall afternoon.
5. Spend time exploring Tarrytown
Don’t visit Sleepy Hollow without spending some time in neighboring Tarrytown. Walk through downtown, visit local shops, grab something to eat, and enjoy the cozy Hudson Valley atmosphere.
Where to Stay Near Sleepy Hollow
Tarrytown House Estate
A historic estate set on 26 acres overlooking the Hudson River. With beautiful grounds, historic architecture, and plenty of fall scenery, it’s an ideal home base for a Sleepy Hollow getaway.
Courtyard by Marriott Tarrytown Westchester County
A comfortable and convenient option close to Sleepy Hollow’s seasonal attractions. It’s a great choice for travelers looking for a modern hotel with easy access to the surrounding area.
SpringHill Suites by Marriott Tarrytown Westchester County
An all-suite hotel offering spacious accommodations, complimentary breakfast, and free parking. It’s a convenient option for couples, friends, and families spending a fall weekend in the area.
Sleepy Hollow Fall Travel Tip
Plan your trip around both Sleepy Hollow and Tarrytown rather than limiting your visit to Sleepy Hollow.
The towns are right next to each other, and combining them gives you more restaurants, shops, hotels, and things to do.
Popular fall attractions and special events can sell out, particularly during October weekends, so purchase tickets and make reservations ahead of time.
Recommended trip length: 2 nights
3. Vermont
Best for: Fall foliage, scenic drives + cozy New England towns
If your dream fall vacation includes colorful mountains, covered bridges, charming small towns, cider donuts, farm stands, sweaters, and scenic drives, it’s hard to beat Vermont.
Vermont is consistently considered one of the best places to see fall foliage in the United States, and for good reason.
During September and October, the state’s mountains, forests, farms, and small towns become covered in shades of red, orange, yellow, and gold.
Unlike Salem and Sleepy Hollow, Vermont doesn’t need a packed itinerary.
The road trip itself is part of the experience.
Give yourself time to drive, stop at viewpoints, explore small towns, visit farm stands, take photos, and pull over when you see something interesting.
5 Best Things to Do in Vermont in the Fall
1. Take a scenic fall foliage drive
One of the best things to do in Vermont during fall is simply DRIVE.
Route 100 is one of Vermont’s most famous scenic roads, but there are beautiful mountain roads, scenic byways, and small-town routes throughout the state.
Build extra time into your itinerary for spontaneous stops and viewpoints along the way.
https://www.visit-vermont.com/state/foliage
2. Visit Vermont’s covered bridges
Vermont is famous for its historic covered bridges, and they look even more beautiful surrounded by fall foliage.
You’ll find approximately 100 historic covered bridges throughout the state, making it easy to incorporate several into a Vermont fall road trip.
Visit Vermont’s Covered Bridges: https://vermontvacation.com/things-to-do/trip-ideas-itineraries/covered-bridges/
3. Explore Woodstock and Stowe
If it’s your first fall trip to Vermont, Woodstock and Stowe are two destinations worth adding to your itinerary.
Both offer quintessential New England charm, restaurants, shops, beautiful scenery, and easy access to outdoor activities and fall foliage.
Viator Tour: Small Group Tour in Stowe, Vermont
4. Get outside
You don’t have to be an experienced hiker to enjoy Vermont’s fall scenery.
Go for a foliage hike, walk a recreation trail, take a scenic gondola or chairlift ride, visit a viewpoint, or simply spend an afternoon exploring outside.
11 Best Hikes & Views in Vermont; All Levels
5. Eat your way through Vermont
This is NOT the trip to skip the snacks.
Stop at farm stands, farmers markets, country stores, cider mills, and local restaurants.
Try fresh apple cider donuts, Vermont maple syrup, local cheese, baked goods, and other seasonal specialties along the way.
Viator Tour: Small Group Wine & Cider Tour in Vermont
Where to Stay in Vermont
Woodstock Inn & Resort | Woodstock
A quintessential New England resort located in the heart of Woodstock Village. Expect beautiful grounds, cozy accommodations, dining, a spa, and easy access to one of Vermont’s most charming fall destinations.
The Lodge at Spruce Peak | Stowe
A luxury mountain resort at the base of Mount Mansfield surrounded by beautiful Vermont scenery. The resort offers dining, a spa, an outdoor pool, and plenty of ways to enjoy the mountains during fall.
Green Mountain Inn | Stowe
A historic inn located right on Main Street in Stowe Village. It’s a great choice for travelers who want classic Vermont charm with restaurants, shops, and the village within walking distance.
Vermont Fall Travel Tip
Don’t plan your entire vacation around seeing “peak foliage” on one specific date.
Fall colors change at different times depending on location, elevation, temperatures, and weather conditions.
Instead, turn your Vermont getaway into a road trip so you can explore different areas and elevations throughout your stay.
For a first-time fall visit, consider spending two nights around Woodstock and two nights around Stowe, with plenty of time for scenic stops along the way.
Recommended trip length: 4–5 nights
Which Fall Destination Should You Choose?
Can’t decide where to go?
Choose Salem if… you LOVE Halloween, witches, ghost tours, history, costumes, and being right in the middle of the spooky-season action.
Choose Sleepy Hollow if… you want spooky fall vibes, historic charm, Halloween activities, and an easy weekend getaway in New York’s Hudson Valley.
Choose Vermont if… your dream fall vacation involves colorful foliage, scenic drives, charming New England towns, covered bridges, cozy hotels, and absolutely no problem stopping for multiple cider donuts.
And if you’re thinking…
“Okay, I want to go. I just don’t want to PLAN all of this.”
I can help with that.
Let Me Help You Book Your Fall Getaway
As a Fora Travel Advisor, I can help you book your fall trip, from finding the right hotel for your travel style and budget to helping you narrow down where to stay.
When you book your hotel through me, you may also receive special travel advisor perks at participating properties, which can include benefits like hotel credits, complimentary breakfast, room upgrades when available, and other amenities.
Whether you’re planning a spooky weekend in Salem, a Sleepy Hollow getaway, a Vermont fall foliage road trip, or somewhere completely different, I’d love to help you turn that trip idea into an actual vacation.
🍂 Ready to plan your fall getaway?
Contact me here: https://www.foratravel.com/advisor/alessia-tenebruso
