The Ultimate Guide to October Getaways

road in the fall, fall foliage, fall leaves, new england in the fall

The Ultimate Guide to October Getaways

Before the frantic holiday travel begins in November, it can be nice to take advantage of October's beautiful weather – not to mention, Columbus Day weekend – and take a short trip away. In case you aren't sure where to go, our October travel guide below covers our favorite destinations from coast-to-coast, whether you're traveling with friends, a partner or happily solo.

Mountain Club, Loon Mountain Hotels, Loon Mountain

Mountain Club on Loon

If you live in Boston, go to...New Hampshire. 

New England is the leaf peeping capitol of the United States, and there's no better place to do it than New Hampshire. Go for a drive along the famous Kancamagus Highway (known as "The Kanc"), where you'll get a clear view of the White Mountains, the Swift River and other natural sites. There aren't any hotels (or any development at all, for that matter) along the Kanc, but if camping is not your style, we recommend the Mountain Club on Loon. A ski resort in winter, Loon is the perfect perch to stay while exploring the area, and there are plenty of fall activities like mountain biking, mountaintop yoga, Ziplining and even an Oktoberfest celebration on October 12-13. At the resort itself, you can enjoy farm-to-table food at the restaurants, or take a relaxing break in the spa and wellness center.

If you live in New York, go to...New York! 

Ok, we know this may seem like a cop-out, but hear us out. The Fall is really the one time of year when New York is not unbearably hot, cold or rainy. And so we recommend taking full advantage of this Goldilocks season with a staycation. Check out our full guide to the city this October, and if it's delicious food you're after, take a look at our guide to what to eat in New York right now. If you're visiting New York from another city this October, consider staying in the new Equinox Hotel in Hudson Yards; Related residents receive special savings and you're going to want to check out the new restaurant, Electric Lemon.

The Grand Hotel, Grand Hotel Michigan, Grand Hotel

The Grand Hotel

If you live in Chicago, go to...Upper Peninsula, Michigan. 

Though the Northeast may have the most famous foliage, Upper Michigan's is not too shabby either. And as an added bonus, go on the right weekend, and you might actually be lucky enough to spot the Aurora Borealis, which starts becoming active around the Autumnal Equinox. As its name implies, the Grand Hotel on Mackinac Island may very well be one of the state's most impressive and luxurious hotels, boasting the world's longest porch, which overlooks Lake Huron and the Straits of Mackinac. Even better, the resort is offering special rates during the Fall months when it's slightly less crowded (though no less beautiful). As for food, you have to try dinner in the main dining room of the Grand, where everyone is required to dress up, while being serenaded by the Grand Hotel Orchestra.  There are also plenty of more casual spots to dine outside of the hotel, like Pink Pony, where you can get a colorful cocktail to accompany your burger. And for dessert, head to Sadie's Ice Cream Parlour, which sells 24 flavors of ice cream made in Michigan, and is located in the Grand Hotel (though you don't need to stay there to get a scoop).

If you live in California, go to...Santa Barbara. 

October is a busy month in Santa Barbara, where events are happening all month long. Is food and drink your passion? Head to the Santa Barbara Harbor and Seafood Festival on October 12, where you can enjoy fresh fish and chat with the fishermen who caught them. As part of the event, the Santa Barbara Maritime Museum will be hosting a special wine and seafood pairing event on its patio overlooking the harbor, with local wines. If architecture is your speed, check out the ArchitecTours 2019 on October 5, where you can take a self-guided tour of the best architectural projects in Santa Barbara. And for any cyclists out there, the famous Ride Santa Barbara 100 takes place on October 19, with stunning bike paths along the water, with four courses suited for a range of abilities. As for accommodations, you can't beat the classic Belmond El Encanto; in fact, the five-star hotel is so beautiful and secluded, we wouldn't blame you if you chose to spend your entire long weekend cocooned by the pool, overlooking the ocean.

Annapolis, Maryland, City Dock in Annapolis, Dock in Annapolis, Annapolis sunset

The city dock at Annapolis, Maryland (credit: Charlie Stinchcomb / Flickr)

If you live in DC, go to...Annapolis. 

The quaint seaside town of Annapolis is the perfect place to go in October, when the summer crowds have long departed. For boating enthusiasts, the United States Powerboat Show – running October 3 -6 – is a must-see, as it's the oldest and largest in-water powerboat exhibition in the world. It's hard not to escape the sea in Annapolis, thanks to its distinction as the "sailing capital of the United States,"; rent a kayak, canoe or paddle-board for the day and explore the Chesapeake, or go for a sail boat tour. Luxury resorts aren't exactly abundant in this modest town, but the Westin Downtown is conveniently located to wherever you need to go. And if you're looking to stay further outside the town, the Inn at Horn Point is a charming B&B from 1902, located directly across the harbor from downtown in Eastport. The comfort food restaurant Preserve is a popular spot to hit, serving up unique takes on traditional Maryland food like Crispy MD Blue Catfish & Chips. And the casual spot Boatyard Bar & Grill may not be fancy, but it boasts offering the best crab-cake in Maryland, according to the Baltimore Sun. High praise indeed, and a major reason why the spot is a must-visit for anyone coming to the town.

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