6 Fall Vacation Destinations & How to Dress for Them

6 Fall Vacation Destinations and How to Dress for Them

Whoever decided that summer is the height of travel season needs to think again. Fall presents rich opportunities for travel each year, from the traditional jaunt to a bed and breakfast in a cute New England village to the final (and very non-crowded) visit to your favorite beach town.

Now that you've hopefully been won over, there's just one more thing to consider: how will you be dressing? Consult our list below to get our top fall vacation destinations and our thoughts on how to dress for each.

1. The Leaf-Peeping Tour

A northern expedition to take in the changing spectrum of fall foliage may be the most obvious entry on this list, but it doesn't make the experience of a leaf-peeping tour any less magical.

We'll start with the obvious. Wear a pair of pants—whether that's jeans or yoga pants—that you consider being the most comfortable, because you may be confronted with traffic on the way to the most popular of leaf-peeping destinations, no matter how rustic and rural the surroundings. Make sure that you’re layering, as temperatures in the fall can swing dramatically. For the top layer, you should of course consider a flannel shirt, because no other article of clothing so communicates the idea of fall. In case it happens to grow chilly at night, be sure to have either a cotton sweater or a fleece jacket on hand. Also think about bringing along a hat, gloves, and a scarf. You never know when things might become a bit chilly, and it’s better to be prepared. 

For your feet, a warm pair of socks and a sturdy set of boots would be best. Make sure your boots and socks are comfortable for walking around. You don’t want blisters ruining your jaunt.

2. The New England Bed and Breakfast

So you've committed to spending a long weekend at some charming, family-run bed and breakfast in Vermont, Maine, New Hampshire, or some other state beloved for its changing fall foliage and abundance of maple syrup. You have made a great choice!

Bed and breakfasts, and the towns that surround them, are never formal affairs, so you should have no problem adopting a pair of jeans and a turtleneck as your uniform while you explore the town. In case it gets a little cold, you might want to have a fleece jacket and a hat within reach.

However, don't forget about the first word in "bed and breakfast." As cute as the nearby antique shops and farmer's markets may be, you should make the most of a lazy morning at least once during the weekend. So don't forget to pack your favorite pair of sweatpants and flannel pajamas: you deserve it.

3. The Apple Orchard

A visit to an apple orchard is a must-do for any fall itinerary. As it's an outdoor activity that might get your hands a little dirty, dress in something simple like a pair of jeans and a flannel shirt. Depending on the weather, bring along a rain jacket in case rain clouds are spotted on the horizon, or a fleece jacket and cotton sweater if the mercury is predicted to drop. Be sure to bring hardy footwear that can navigate tree roots and the occasional patch of mud: a good pair of winter boots is ideal.

Lastly, don't forget about the most important part: the apple collection. You can bring a canvas tote to hold your bounty and transport it home safely and in a sustainable way.

4. The Post-Season Beach Rental

Anyone with a favorite beach town knows that they can become frightfully packed each July and August. Instead of fighting the crowds for a spot in the sand, stay clear of the summertime congestion altogether and opt for a visit during the post-Labor Day season. Consider a swimming suit, but make sure you take along a cover-up or even a swimming shirt in case things get too chilly. 

From mid-September, to early October you may indeed have warm weather, but there's also a good chance that temperatures will dip after sunset. For that reason, make sure that you have a cashmere sweater as a contingency plan to deal with chills.

5. The Spa Trip

Spas may not be connected to fall in any significant way, but there's no reason why an autumnal visit to your favorite spa won't be just as satisfying as it proves in winter, fall or summer. Indulge yourself with a spa visit, and bring your comfiest activewear in the form of yoga pants and easy loungewear like sweatpants, pajamas, or a tunic.

6. Ski Lodge During Mud Season

Alright, hear me out. While a ski lodge might not be as amazing during mud season as it is during the winter months, it’s still worth checking out. Mud season at ski resorts means lower prices at resort hotels and you might have the place to yourself. While you probably won’t see snow, you’ll still be able to enjoy beautiful mountain views and some of the amenities you might not have used if you were just there to ski.

For this trip, consider taking along your favorite cashmere sweater and a pair of jeans. Cashmere can be dressed up or down and is a great way to be cozy while staying comfy and warm. Pair that with your favorite jeans and some women's comfort shoes that you don’t mind getting a little muddy, and you’ll be set.

No matter what kind of fall trip you decide to take, you’ll have a great time, and be comfortable in the outfits you’ve chosen. Don’t forget to be prepared for the weather to change, though. Fall can show off some of the most comfortable weather of all seasons, but it is volatile–so always have a backup outfit ready.


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