Small Town Charm: The Best Fall Vacations & Our Fall Adventure Packing List with Manzella

This fall vacations post has been sponsored by Manzella. All thoughts and opinions are my own.

Ahhh fall travel. Who else absolutely loves traveling during the fall season more than any other season throughout the year? Fall landscapes are just so dreamy and idyllic—full of color and texture and life. It always inspires me to get out there and see and visit as many new destinations or old favorites as possible throughout the season. Which is why, today, we’re sharing some of our very favorite cozy, charming, small town travel destinations for the fall season! And we’re getting a little help from one of our very favorite form-meets-function travel essentials we never leave home without throughout the fall: our trusty Manzella gloves. We hope this list inspires your fall wanderlust and maybe even gives you some new insight into unique fall travel ideas you’ve either never considered before or need to finally check off of that list. As for the focus on small town fall travel, that’s just what we do here on Love + Specs! We live for the cottage-cozy charm and when we travel, that’s what we seek out and love the most—which happens to be perfect for capturing those fall feels properly, don’t you think?

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First things first, though. I should be totally honest with you guys and admit that half of my love for charming fall travel packed with fun outdoor activity of all kinds has to do with my love for the opportunity to finally bust out my favorite cozy fall gear. Anyone else with me? What can I say… I love to bundle! I love spending as much time out in that fresh fall air as possible, diving into all the adventure, activity, and hands-on fun I can find. In order to do that comfortably, I have to have great gear with me that adds warmth and can stand up to whatever activity comes my way. Style, warmth, comfort, durability, flexibility—my recipe for fall travel gear greatness! That’s why I fell so hard in love with these Manzella Cable Knit Outdoor Gloves. They totally fit that bill, are absolutely adorable in this classic grey cable knit, and they have the softest brushed knit lining ever to keep my hands comfy and super warm. They’re the first thing I pack for fall travel adventures.

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And all of that goes double for Chris, who literally cannot find his chill when he’s hanging out in the great outdoors in the fall. When we travel, Chris’ already adventurous spirit goes into overdrive. That’s why gifting him a great pair of durable, versatile gloves that he’ll love for a lifetime was the perfect way to jumpstart our fall travel. Finding great gift inspiration for guys can be tough. I always keep little notes in my phone of the activities Chris loves most paired with the essentials he’s missing that would help him enjoy each activity more. I also like to keep track of the adventure essentials he’s worn out completely that could stand to be replaced. On that list for the last year or so was a really durable, warm pair of gloves that were sleek and stylish enough to wear for everyday activity. They also had to be able to stand up to a lot of wear and tear throughout our travel adventures, outdoor activities, and work around our home. I zeroed in on these Manzella Ranch Hand Touchtip Outdoor Gloves (you can find them here!). They’re super warm, touch screen compatible, have a waterproof, breathable insert, and feature a reinforced palm for extra durability. So basically, they’re 100% Chris lifestyle approved! They’re also really sleek and flexible, as you can see. This means that Chris can wear them for fishing and other outdoor activities and work that requires warm but mobile hands. To say he’s in love is an understatement. I think he was actually shocked by my gifting genius, and now these are the first thing he grabs when he’s packing for trips this season. Win!

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Now that we have our packing essentials covered, it’s time to get out there and check some epic fall travel destinations off of this list! We had so much fun compiling this list. That’s in large part due to the fact that we received so many amazing recommendations and so much useful, exciting insight from you guys when we crowdsourced your favorite charming fall travel destinations from around the country on Instagram Stories! Your responses were so enlightening. We just loved hearing all about your favorite fall travel destinations across the U.S. and why you especially love them during this special season. There were so many charming little small towns from around the country in there that we had never heard of before, so thank you guys for jumping in on this and submitting your recommendations. Variety is the spice of life, and you guys totally delivered the (pumpkin) spice on this one!

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Now, we only had a few requirements for locations to be considered for this list. After that, when we started talking lodging, dining, scenery, and all of the other things that make travel in general really memorable, that’s when the list got refined into the winners you see here. But our basic requirements for fall travel greatness are as follows:

1. They have to have that small town charm. There are about a thousand amazing destinations all around the country that would be completely magical in the fall, but this list is solely comprised of locations that are either small towns or regions comprised of several charming small towns. Because that’s what we do here on Love + Specs. Small town charm!
2. They have to offer a delightful combination of traditional fall activity as well as outdoor adventure. If the location also happens to be heavy on the fall foliage and color spotting, that definitely helps their case.
3. They have to be located in a climate that offers a taste of traditional fall weather. That’s just non-negotiable. If I can’t sip a hot apple cider comfortably in the location’s climate, it’s a no-go.

So without further ado, we present to you the very best of charming, small town fall travel from across the U.S. These destinations will fill your fall season with all the fall activity, color spotting, and cozy outdoor adventure you can handle!

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The Best Small Town Fall Vacation Destinations in the US

FLAGSTAFF, ARIZONA

If you think Arizona is all about desert and red rocks, this uber-charming mountain town set amongst Ponderosa Pines and glittering Aspens will quickly change your mind about that! An adorable, historic little college town, Flagstaff is the perfect place to cozy up for chilly fall temps and endless outdoor adventure with breathtaking views. It’s also quickly becoming known for its abundance of stylish, rustic vacation rentals—perfect for fireside fall snuggling! Its quaint downtown area is full of unforgettable dining options and unique local coffee shops that make it feel especially fall-perfect. Flagstaff also happens to be just a short, extremely scenic 20-minute drive to picturesque Sedona, which is another worthy fall getaway destination on its own. As you can see from our snaps, we went straight from bopping around charming downtown Flagstaff and grabbing a bite to sweeping scenic views and outdoor adventure in just a short, 10-minute drive, which is pretty awesome. So, what was the coolest part of our fall getaway to Flagstaff this year? While loading up the car at sunset after fishing, we kept hearing these funny sounds off in the distance that we thought were coyotes howling. As soon as we drove down the road a bit, we saw a photographer posted up on the hill capturing what we quickly realized was a huge herd of elk out in the most gorgeous field! So, we pulled off and got out to take it in. It was nothing short of spectacular. We also got a better listen to their cool elk call again now that we were closer, which made for one of the most memorable sunsets we’ve ever had together. Fall magic!

NORTHERN MICHIGAN

We’ve said it before on here and we’ll say it again for the people in the back: if it’s the most charming small-town fall adventures and color tour action you seek with untouched beauty for miles, look no further than the great state of Michigan! Specifically, the region at the tippy top of the lower peninsula that Michiganders lovingly call “Up North.” Northern Michigan is home to the most magical, charming small towns overflowing with cozy, inviting pitstops for tasty local treats, outdoor activity in abundance, and some of the best fall color spotting and scenic routes in the country—the famous 27-mile-long Tunnel of Trees on M-119 being a highlight. Pro Tip: it’s hard to imagine a more cozy, fall-perfect getaway than Hotel Walloon, which would be an unforgettable location to take in the fall foliage and activity on its own. The hotel also happens to be nestled in a centralized spot in the region that makes it an ideal hub for taking day trips to all of our favorite charming northern Michigan towns. 

The Best Small Towns in Northern Michigan:

Traverse City, Michigan

Petoskey, Michigan

Harbor Springs, MI

Leland, MI

Saugatuck, Michigan

THE BERKSHIRES, MASSACHUSETTS

Another incredible fall foliage spotting destination, this historic mountain region is home to everything the East Coast does best when it comes to those fall feels we all love. They pretty much wrote the book on fall fun (pun totally intended because this region is home to Louisa May Alcott’s “Orchard House,” which was the backdrop for Little Women). Made up of a collection of several small towns that all offer their own brand of historic charm, the Berkshires offers creative dining options, all of the traditional fall activities you could ever want (pumpkin patches, apple orchards, corn mazes, etc.), and outdoor adventure like hiking and biking galore. And it’s all paired with an abundance of charming and memorable lodging options, ranging from quaint B&Bs to unparalleled spa retreats. If you haven’t experienced this area in the fall, this one should definitely find its way to the top of your list!

The Best Small Towns in the Berkshires:

Lenox

Great Barrington

Stockbridge

West Stockbridge

Williamstown

UPSTATE NEW YORK

This was yet another reader reminder that absolutely had to land on this list because it’s just a fall requirement, period! This is also another East Coast region that basically defined our country’s love for fall fun. You can’t beat the plethora of apple orchards and cider mills, farms, scenic drives drenched in fall foliage and vibrant fall colors, historic small towns brimming with charm, picturesque lakes, and world class dining and lodging of all kinds. If it’s the best of what fall has to offer you seek, from scenery to small town charm, Upstate New York is basically a sure thing. Mohonk Mountain House near New Paltz, NY is a personal family favorite and a one-of-a-kind experience that would only be enhanced by this magical season.

The Best Fall getaways in Upstate New York:

The Catskills

Lake Placid

New Paltz/Mohonk Lake

Hudson Valley, NY

LEAVENWORTH, WA

Full disclosure, I’d never heard of Leavenworth until one of our amazing readers chimed in with this delightful recommendation and now I’m dying to visit! This charm-packed Bavarian “village” in central Washington looks like it’s ripped right out of The Sound of Music. Not only known is it known for its spectacular fall color show but it’s surrounded by mountains, rivers, and wildlife galore—perfect for fall adventure of all kinds. Plus, the town itself offers all sorts of fun fall activity all season long, including all the kitschy Bavarian fall festival fun you can handle. Sign me up! 

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SALEM, MA

Yet another amazing reader recommendation that should easily, without question, be at the top of your fall getaway list. Salem, MA is packed with traditional fall fun of all kinds, with its somewhat spooky history at the center of its appeal in this particular season. Its quaint, charming, historic downtown is perfect for cozy fall walks, candlelit ghost tours, and other haunted happenings that are enough reason to plan an epic fall visit on their own. Don’t forget that this particular region of the country is also perfect for fall color tours and other quintessential “fall” activities and adventures of all kinds. Salem is at the very top of my personal fall getaway list, witch (see what I did there?) means it’s high time I made it happen!

STILLWATER, MN

Oh, Minnesota. Minnesota has about a thousand charming small towns that perfect for fall activities and adventure scattered throughout the state. The quaint riverside town of Stillwater is especially magical this time of year. Bonus: its close proximity to the Minneapolis/St. Paul area makes travel as convenient as can be. Not only is this an idyllic location for catching the fall colors in the crisp, Midwest fall air but there are so many quintessential Midwest fall activities to enjoy in the surrounding region, like pumpkin patches, corn mazes, hayrides, cider mills, and so much more! There’s also an abundance of fun antique shops to explore in the downtown Stillwater area that aren’t to be missed, if you’re into that sort of thing. Which we totally are. 

TELLURIDE, CO

Another amazing recommendation from one of our readers that I’m ashamed to say I’d completely forgotten about. Telluride is known for its historic downtown packed with Old West charm and endless opportunity for outdoor adventure in the surrounding area in any season but in the fall, this cute Colorado town is especially magical. You should certainly catch the fall colors in the surrounding San Juan Mountains via a fun ride on the gondola, but the fall delight doesn’t start and end there. There’s hiking, biking, fishing, Jeeping, and so much more at the ready, paired with some amazing dining options that make for the coziest, tastiest end to the perfect fall day. If you’re looking for a truly unforgettable and elevated experience, nearby Dunton Hot Springs or even their new downtown Telluride property located inside a completely renovated old house, Dunton Town House, are just about as romantic, luxe, and cozy-fall-perfect as it gets. 

PARK CITY, UT

Sure, Park City’s known as a winter wonderland and is home to Sundance but in the fall, this charming little mountain town comes alive with fall color, coziness, and outdoor activity. Bonus: this fun Old West town is so much more walkable in the fall than in the frigid winter, which is a huge plus. It’s also just a quick, convenient drive from the Salt Lake City airport & is known for its plethora of memorable accommodation options, ranging from the coolest traditional rustic lodges, to luxury retreats, to charming B&Bs—all at off-season prices! The activity offerings are awesomely varied, too, so in just a day you could hike, bike, fish, take a scenic drive to catch the fall colors, join a distillery tour, and cap it all off in a world-class restaurant. Fall bliss!

STOWE, VERMONT

I feel like at this point we’re all aware that Vermont is a hotspot for fall delight, in large part due to a stunning display of fall foliage, but this charming small town is also full of fall activity, relaxing lodging options, cozy local hangouts, and tasty, chef-driven cuisine galore—making it the perfect spot to snuggle up, explore, and enjoy all things fall. Between the cider mills, the scenic drives alight with fall colors, gondola rides up the mountain, and just about every other quintessential fall activity you can think of, I’m convinced that in the dictionary next to the word “cozy” is a picture of Stowe. That said, Stowe is just one of Vermont’s charming small towns that puts on quite the show in the fall, so below are a few more Vermont gems worth a fall visit. 

The Best Small Towns in Vermont:

Woodstock

Manchester

Dorset

Grafton

BONUS ROUND

Hungry for more? We couldn’t let the fall travel love stop there, and neither could our readers! So, below are a few more small town fall getaway options, shared by our readers to add to your fall travel bucket list. We’d also love to keep this fall travel conversation going, so make sure to drop your favorite fall travel destinations in the comments below!

Bar Harbor, Maine

Canon Beach, Oregon

Walla Walla, Washington

Asheville, North Carolina

Cherokee, North Carolina

Big Cedar Lodge, Missouri

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