You’ve come to the right place if you’re looking to plan a trip to either Salem, MA or Sleepy Hollow, NY this October, but can’t decide which to visit. Having been to both, and also currently living in both Upstate New York and Massachusetts, I’ve got so much insight to share with you, including crowds, things to do, and the biggest differences between the towns.
By the end of this post, you’ll hopefully have a good idea on which town suits your plans and preferences the best. So, let’s get started!
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Biggest Differences Between Salem & Sleepy Hollow
Okay, so let’s start with the major differences between both towns. While Salem and Sleepy Hollow are both small towns with awesome Halloween/fall vibes, the biggest difference are:
→ Salem has more to do than Sleepy Hollow.
→ Sleepy Hollow is very, very small. In fact, half of the best things to do when visiting are in the neighboring town of Tarrytown, plus a few things to do outside both these areas.
→ There are no hotels right in Sleepy Hollow. Most people stay in Tarrytown or another nearby town. Salem, however, has many hotel options right in town that are walkable to all the top attractions. I also much prefer the hotel options in Salem over the ones in the Tarrytown area.
→ Sleepy Hollow itself is very walkable, but since many of the top things to do are outside of town, you may want to consider driving, as places like the Great Jack-O-Lantern Blaze and Washington Irving’s Sunnyside estate are not walkable from Tarrytown/Sleepy Hollow.
→ Salem has a very distinct New England vibe, as expected since it’s in New England 😉 If you’re a fan of Hocus Pocus, you’ll probably love Salem, as the atmosphere is very similar to the movie. In fact, some scenes from the movie were filmed right in Salem. Sleepy Hollow definitely has a quaint Upstate NY vibe, and sits along the Hudson River – it fits right into the Hudson Valley atmosphere.
Similarities Between Salem & Sleepy Hollow
Now that you know the key differences, let’s talk about how both towns are similar:
→ Both Salem and Sleepy Hollow have a distinct Halloween/fall vibe that’s very prevalent. I would say Salem really runs with the Witch City theme more than Sleepy Hollow runs with the Headless Horseman narrative. But you won’t find any shortage of Halloween fun and decorations in either place. Sleepy Hollow’s neighboring town of Tarrytown also does a great job making the town feel exciting and special in October.
→ Both towns have parties and events in October.
→ Both have quaint downtown areas with shopping and dining. Sleepy Hollow’s is very, very small compared to Salem, but Tarrytown has a bit more to offer in this department, so you have some options when visiting Sleepy Hollow. Salem is packed with shopping and dining options.
→ Both towns get very crowded in October, especially the weekend of, or before, Halloween.
So, Which Is Better To Visit In October?
Overall, my pick goes to Salem. And this is completely unbiased, even though this is a New England travel website 😉 I’ve lived in Upstate NY most of my life, and even went to college in the Hudson Valley, so I absolutely love NY, too.
But in general, I think Salem makes for a better Halloween destination, especially if you have longer than a day. There’s just so much more to do and see, and lots of options in terms of tours and activities. You’re also not far at all from Boston and other nearby coastal towns like Marblehead, Rockport, Gloucester, Newburyport, etc.
That said, Sleepy Hollow and Tarrrytown are also a lot of fun. While I don’t think you can really go wrong with either choice, it’s good to know that there are fewer things to do in Sleepy Hollow/Tarrytown, and this area isn’t quite as walkable as Salem. Sleepy Hollow was so much smaller than I expected on my first-ever visit, and while you can easily walk between Tarrytown and Sleepy Hollow, you’ll need to drive to other attractions.
Once you arrive in Salem, however, you really don’t ever need your car, unless you want to leave town. Even then, there’s a train station that gets you to other towns along the coast.
There’s also just something about a small New England town in October. Between the historic salt box and Colonial-style houses in Salem, plus picturesque side streets, the fall vibes are truly on point.
I honestly love both, but I do have a slight preference for Salem, and usually recommend it to visitors, too. If you can visit both, I’d recommend that so you can decide for yourself!
Best Things To Do In Salem, MA In October
Take a spooky tour, of course! There are so many options in town, and this is such a great way to learn about the history, ghost lore, and lots more. I recommend this History & Hauntings tour for a little bit of everything, and this Voodoo, Vampires & Ghosts tour if you’re looking to get even more goosebumps on your excursion. If you’re a Hocus Pocus fan, this Hocus Pocus Filming Locations tour is also a lot of fun.
Visit the historic sites, including the House Of The Seven Gables, Salem Witch Trials Memorial, the Witch House, the Salem Maritime National Historic Site, and Ropes Mansion, to name a few.
Walk Chestnut Street, which is often named one of the prettiest streets in the entire U.S.
Attend one of the Halloween parties, with different ones taking place throughout October. The biggest party is the Official Salem Witches Halloween Ball, which takes place on Halloween night each year.
Get the famous lobster martini at The Lobster Shanty.
Visit the local shops. Some of my favorites are District Trading Company for non-cheesy Salem apparel, Spruce Home, and Oak + Moss.
Explore The Peabody Essex Museum.
Visit Ye Olde Pepper Companie, the oldest candy shop in the country.
Psst! I have more detailed posts on Salem, including a Salem, MA day trip guide, the best time to visit Salem, if you’re looking for more info 😉
Best Things To Do In Sleepy Hollow In October
The Great Jack-O-Lantern Blaze in Croton-on-Hudson. This is about a 20-minute drive from Sleepy Hollow, and one of the top attractions in the area during the month of October. You’ll find more than 7,000 lit Jack-O-Lanterns in impressive displays for the perfect fall experience.
Visit the shops along Main Street in Tarrytown. There are some cool places to check out here, including Muddy Water Café, Main Street Sweets, and Transom Bookshop, where you can pick up your own copy of the Legend of Sleepy Hollow.
See the Old Style Horseman Bridge in the Sleepy Hollow Cemetery, which is also where you’ll find Washington Irving’s grave. While this bridge isn’t the official headless horseman bridge that was made famous in the book, it’s a bridge that just has headless horseman vibes. The actual bridge is located on Broadway, which is a busier street in town.
See the Old Dutch Church right by the cemetery, which is where the Van Tassel family from the Legend of Sleepy Hollow are said to be buried.
Explore Philipsburg Manor, a living museum dedicated to into 18th-century colonial life. The preserved site features historic buildings, a working water-powered gristmill, and costumed interpreters who share interesting facts about the manor and its history.
Tour Sunnyside, Washington’s Irving’s home. Even if you’re not a history buff, the grounds and house have a wonderful storybook setting along the river. Visitors are allowed access inside the Dutch-style home to explore rooms filled with Irving’s personal belongings. You’ll also come across costumed guides that share fun facts about the house and the Irving family.
Attend the Sleepy Hollow parade and block party for ultimate Halloween fun. The parade and party typically take place the last Saturday in October, and the block party is held outside in the evening with food, drinks, and live music.
Stroll the riverwalk path to see Tarrytown Lighthouse. The riverwalk is a nice escape from the crowds, and the lighthouse is a fun one to check out!
Take a candlelit tour of Lyndhurst Mansion, called Lyndhurst After Dark. Not only is this a fun, spooky tour to take, but during the candlelit tours, visitors are exposed to more of the darker sides of the mansion’s history.
Where To Stay In Salem
Hawthorne Hotel: My personal favorite place to stay in Salem. The location is central to all the top sites, and the hotel itself is very beautiful and historic. It’s even said to be haunted! I’ve never had any paranormal experiences during my stays, though. It’s also one of the few hotels in Salem with on-site parking.
→ Click here to check rates & availability at the Hawthorne Hotel in Salem
The Hotel Salem: Also in a great location, this hotel is home to the town’s only rooftop bar. Inside, you’ll find an upscale and funky vibe that’s perfect for exploring this unique destination.
→Click here to check rates & availability for the Hotel Salem
Salem Waterfront Hotel & Suites: Just down the street from the Hawthorne Hotel, and also is a great location to explore by foot. They also have on-site parking for added convenience.
→ Click here to check rates & availability for the Salem Waterfront Hotel & Suites
Where To Stay Near Sleepy Hollow
Just a reminder that there are no hotels in Sleepy Hollow proper, and you’ll have to find a hotel in Tarrytown or another nearby town. Unfortunately, not many of them are stand-outs, which is one of the bigger downsides to visiting. Here are my picks for where to stay:
Westchester Marriott: You’re only about a 10-minute drive to Tarrytown from here, and bonus points if you have loyalty with the Marriott brand to use and redeem points for your stay.
→ Click here to check rates & availability at the Westchester Marriott
Tarrytown House Estate: People tend to either love or hate this property, and full-disclosure, I’ve never stayed here (because it’s always been booked when I’ve visited, which is a good sign!). This historic estate has a lot of character, and books up fast during the month of October. It’s about a 12-minute drive to the central part of Tarrytown. I would check out the reviews for yourself to see if you want to give it a shot – I personally hope to stay here someday!
→ Click here to check rates & availability at the Tarrytown House Estate
SpringHill Suites: Also a Marriott property that’s not far from the Westchester Marriott, which means it’s only a 10-minute drive to Tarrytown.
→ Click here to check rates & availability at the SpringHill Suites
Quick Guide: Answering Your FAQs On Both Towns
Didn’t want to read the whole post? No worries! Here’s a breakdown of some of the most common questions I’m asked about the two towns, and also answering some other things I haven’t covered in the post:
Is One Town Easier To Get To Than The Other?
Not really, so I wouldn’t solely base your decision on this factor. You can easily drive to Tarrytown to visit Sleepy Hollow, or take a train from Grand Central in NYC.
For Salem, you can also drive there, with lots of parking options available, or take the train from Boston’s North Station.
It’s good to know that both places have parking options, but parking is a challenge on weekends in October. You really want to get there early, especially if it’s the weekend of, or before, Halloween.
Is There More To Do In Salem Or Sleepy Hollow?
Definitely Salem. There are some really fun things to do in Tarrytown and Sleepy Hollow, too. However, I would say there are a lot more options in Salem.
Are Both Towns Walkable?
Salem is very walkable. Once you arrive, you don’t really need a car unless you want to explore other nearby towns. Almost everything is within 1-2 miles at most from one another. Most attractions are within a mile of each other.
Sleepy Hollow is very walkable because of its size. However, there’s not a ton to do in town, and many of the top attractions are located in Tarrytown, or other areas that require a drive. These include the Great Jack-O-Lantern Blaze, Washington Irving’s Sunnyside Estate, Lyndhurst Mansion, Kykuit, the Rockefeller Estate, etc. While some of these places you can walk to from Sleepy Hollow/Tarrytown, they’ll be over 2 miles each way, with some being much more than that.
You can, however, walk from Tarrytown to Sleepy Hollow. It takes about 20 minutes each way, if you park near the train station in Tarrytown (which is where I’ve always parked).
Are Both Towns Worth Visiting In October?
I think so, yes! I’ve loved all my trips to both towns in October, and have always had a lot of fun. That said, I also did a lot of research, and knew what to expect, etc. I think level-setting expectations and preparing for crowds is key.
In fact, my first-ever trip to Salem in October years ago was actually not the fun getaway I had been dreaming of – I wasn’t prepared for the crowds, didn’t look into parking ahead of time, and it was stressful because of it. I learned an important lesson that trip! Ever since, I’ve always gone into fall trips more prepared, and it allows you to soak in the magic every step of the way.
But in general, both towns do a great job with decorations, events, and have great fall scenery. It’s really hard to not be in the Halloween spirit when visiting either town.
Are Both Towns Crowded In October?
Yep! And this is something I never want to sugar-coat. Having been to both the weekend before Halloween, I can say with absolutely certainty that both towns will be very, very crowded. But as mentioned, if you know to expect that going in, and arrive prepared, you can still have a great time.
Is There Fall Foliage In Both Salem & Sleepy Hollow?
Yes. I think you’ll find more foliage in Salem than Sleepy Hollow, but you’ll have a good amount of foliage color in both destinations. Neither are known for their foliage, but it’s definitely there, and adds to the fall ambiance for sure.
Is Salem Too Touristy? What About Sleepy Hollow?
I’ve heard a lot of people online say that Salem is just so touristy, and that’s probably because they really lean into their nickname of Witch City a lot. Yes, there are quite a few touristy stores and such, and yes, you’ll come across a lot of “witchy” shops selling spell-related things. But I’ve honestly never gotten the feeling that it was too much when visiting (and I’ve been many times in October and other parts of the year). I think it’ll come down to your expectations. You should definitely anticipate some level of touristy vibe in Salem, but it’s also pretty easy to look past it to appreciate its history and charm.
As far as Sleepy Hollow, my overall opinion is that it does have a slightly less in-your-face tourist vibe. That said, they also lean into their Headless Horseman connections quite a bit. It just feels a little less obvious than Salem.
Which Is Better For A Day Trip?
Both make for great day trips, and it really just depends on where you’re coming from. Sleepy Hollow/Tarrytown is an easy day trip from NYC, and the Hudson Valley/Westchester areas. Salem is better for those in Boston or nearby.
Both can easily be done as a day trip, and you’ll have enough to do in both places.
Which Is Better For A Weekend Getaway?
I think Salem wins in this category. As already mentioned a few times, there’s just more to do right in Salem, and you can easily fill in an entire weekend just by visiting Salem. Between the tour options, boating tours, historic sites, shops, and Halloween events, there’s plenty to see and do, but it’s also not overwhelming – it’s still a small town, after all 😊 You can also plan to visit other nearby towns if you feel like a weekend is too long in Salem, including Boston, Rockport, Marblehead, Gloucester, and Newburyport.
My first-ever trip to Sleepy Hollow was a long weekend getaway, and we did Tarrytown/Sleepy Hollow/Sunnyside in one day – easily. We planned the other day for visiting some of the historic sites outside of town, combined with the Great Jack-O-Lantern Blaze at night. But we definitely had a lot more downtime in Sleepy Hollow.
You may also enjoy:
- Fall In Massachusetts: Where To Find The Best Foliage
- My Incredible Fall Road Trip Itinerary
- A Guide To Upstate New York In The Fall
That’s A Wrap On Salem, MA Or Sleepy Hollow In October!
And there you have it! My comparison on Salem and Sleepy Hollow in the fall season, and which is better to visit. While my overall pick is Salem because it has more options for things to do, I don’t think either will disappoint if you plan accordingly. There’s a lot of fall fun to be had in both. Happy planning! 🍁🍂
