Guys, after YEARS of taking road trips, getaways, and day trips to New England in the fall season, I’ve really gotten my packing down to a science. I’ve been traveling through this region during foliage season for over 20 years now, and have tried a lot of different clothing options, figured out how to adjust to temperature fluctuations, and how to stay comfortable. I’m also now a part-time Massachusetts resident, so living in New England in the fall season as taught me a lot, too.
I’m so happy I get to take all this experience, and create a list of everything you actually need to pack for a New England fall trip.
In this guide, I’ll share all the must-haves for your trip, including clothes, footwear, hiking gear, and accessories that have made my fall trips a lot easier. I’ll also tell you what you don’t need, which is often just as important.
So, if you’re ready to start packing for your fall foliage trip, I’m ready to help. Let’s jump in!
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Overview Of New England Fall Trip Packing: General Tips
In general, the most important things I always recommend when packing are:
→ Layers to adapt to the changing temperatures
→ Comfortable clothes/shoes
→ Rain gear
If you have these basics, and take nothing else from this post, you’ll be good. But, there are some other things I’ll recommend below that are also worth bringing, depending on how long or short your trip is.
New England fall weather is moody, and the fall season – while mostly what you’d expect – can bring everything from warm days to rain, and in more rare occurrences – snow.
So with that in mind, it’s ideal to pack in a way where you can prepare for any kind of weather New England throws at you. For longer road trips (more than a week), this becomes even more important because you’re more likely to experience fluctuations in weather – especially as you get further into October. But regardless of how long your trip is, it’s still good to be prepared.
Everything You Need To Pack For New England In The Fall
Clothing & Shoes: Keep It Casual & Comfortable
Dress In Layers. So, what do I suggest for outfits to be comfortable in varied weather? I mostly wear jeans, a short or long-sleeved base top (depending on the forecast that day), and a sweater or jacket. That’s it. This formula is so easy to pack with, and has really streamlined my packing.
Jeans are the easiest pants to get away with. Most people find them comfortable, and they can be reworn a few times each trip. They also pretty much go with everything, and can also look nice enough to go out to dinner in.
Base Layer Tops. In the last few years, I’ve been using merino wool t-shirts under flannel shirts and sweaters, and these have made my life on the road so much easier. Merino wool is more of an up-front investment, which is why I held off for so long. But, they really are worth buying, especially if you travel often. I now wear these when I’m hopping on a plane, or traveling anywhere, and they’ve more than paid for themselves.
Not familiar with merino wool? It naturally repels odors, regulates body temperatures, and is moisture-wicking. Because it’s pretty good as repelling odor, my merino wool shirts can be worst at least twice – sometime three times, depending on how, er, sweaty I get.
→ These are the merino wool t-shirts I’ve been using, which are on the more affordable side. My husband also loves these (they have a men’s fit version, too).
→ If you’re looking to invest in the best quality merino wool top base layers, these from Smart Wool are highly-rated online. I haven’t personally tried them yet, but in my research, this was the brand that most people recommended.
Sweaters. This goes without saying, but sweaters are the perfect layering piece for the fall season. I’ll usually pack a couple of pull-over sweaters, and maybe 1-2 cardigans (depending on how long I’m traveling for), and just rewear them. Having that merino wool base layer underneath also helps to prevent your sweaters from getting stinky, so that’s another perk!
Some sweaters I recommend for a fall trip:
🍁 Woodstock Maple Leaf sweater, or the Big Cozy Fall Leaf sweater, both from KJP.
🍁 Fisherman’s Knit sweater from L.L. Bean. This is such a classic style that works really well in New England. I also will layer this with a turtleneck, which looks really cute (note to self, find merino wool turtlenecks 😂).
🍁 Over the years, I’ve also collected sweaters from Old Navy when I’m on a tighter budget, and they always have great options is nice, fall colors.
Flannels. This kind of goes without saying, but flannels are wildly popular in the fall season for a reason, and are perfect for a fall getaway to New England. They can be layered over a merino wool t-shirt, and I also wear that combination when hiking.
🍁 My all-time favorite and most-worn flannels. These are from L.L. Bean, and I love the larger gingham print and fit of these. These have a fitted silhouette, so I would size up to layer over shirts or just for a more relaxed look.
🍁 My other most worn flannel from L.L. Bean: The biggest difference is this one is has a more relaxed fit and is slightly heavier material. I have two of these, and love them, and they come with me every fall trip.
Comfortable Footwear. For a fall trip, I will bring three pairs of shoes: Sneakers, fall boots, and hiking boots. That’s it. Any time I’ve never packed more than that, I’ve always regretted it because I don’t wear anything else.
I like having options for footwear because it helps to keep you comfortable, while also staying versatile in different situations and weather. Sneakers are perfect for most sightseeing, including easy scenic overlooks, walking around towns, and exploring cities.
Fall boots are great to have if you want to wear something other than sneakers out to dinner, and also work if you just want to wear a boot. I mean, it is the fall season, and we all love a good fall boot! For fall boots, I just recommend keeping them flat, or a low, chunky heel. Don’t bring fall boots with heels – it’s just not worth it, and not appropriate for most things you’ll do on your trip, anyway.
Lastly, hiking boots. If you’re planning to do any trails on your trip, you’ll want good hiking boots. Even an okay pair of hiking boots is helpful for easy trails, as the fall season can have slippery trails where the extra traction and ankle support is very, very handy.
My Recommended Footwear For A Fall Trip:
🍁 Adidas sneakers. These are what I’ve been gravitating lately because they’re a classic style that work well in cities, small towns, and pretty much anywhere. I have the collegiate green color, which works well with most all outfits.
🍁 Vessi waterproof sneakers. These are another great sneaker that I wear a lot when I travel anywhere, including fall foliage trips. They’re completely waterproof, so if you’re not planning on doing any hikes or trails, but want something a bit more functional than a traditional sneaker, these are a great option. I got these for my husband and I for a trip to Scotland a few years ago, and now we wear them all the time. I would suggest another color besides the white, though. My white ones pretty much look gray now because of how dirty they get.
🍁 Danner Adrika hiking boots. I really love these as a great, all-around hiking boot. They’re probably not the best for super serious hikers that hit a lot of super challenging trails every season. But, for most people, these work very well. The ankle support is fantastic, they’re comfortable, and waterproof. They’re also on sale right now, and pretty affordable. Plus, Danner is a very reputable brand, so the quality is great.
For fall boots, I would just pick a Chelsea-style or any ankle boot that works well for you. This is so dependent on your personal style, and you may already have a pair that you love. It’s just very important that they’re comfortable, and have a low/chunky heel for stability.
Outerwear: Plus The One Piece I Can’t Recommend Enough For Fall
Waterproof Rain Jacket. This is the one outerwear piece that I never leave for a fall trip without because it’s the most versatile. On years when I’ve left it at home, I regretted it, and years when I’d had it, it’s been a life-saver on rainy days.
The key is getting a true waterproof jacket. If you have one already, you’ll want to make sure it’s not water-resistant. That doesn’t mean waterproof. And in my experience, there’s a difference in how dry it will keep you.
🍁 This is the waterproof jacket I most-often recommend. I own this in the yellow color, and it’s truly waterproof. They often so sales, so while it’s more of an investment, at a sale price, it’s not too bad. It’s cozy and comfortable, and also looks great. It’s a classic style that you can wear anywhere, making it worth the investment.
Of course, if you have a water-resistant jacket already, and don’t want to buy a new waterproof one, you’ll likely be fine. It shouldn’t be torrential downpours every day of your fall trip, and a water-resistant jacket will work for a lot of people.
However, I stress waterproof for most people for a few reasons: It helps if you get caught in the rain on a hike or while out on a trail, or if you have a full day of rain and don’t want to waste it indoors. It just helps to offer that peace of mind that if you do get a rain day, you can still get outside and stay mostly dry.
Another Fall Jacket. In additional to a waterproof rain jacket, I also recommend packing a separate, lightweight fall jacket – but only if you want to. The rain jacket works very well as an outer layer even when not raining, but I personally like having a second option that’s not a waterproof material. This is also nice for nights when you’re going out to eat, or exploring towns in nice weather.
My favorite alternative is a casual Shacket, or a classic barn jacket.
🍁 L.L. Bean Classic Barn Jacket. Love the traditional style of this one, and it’s flannel-lined.
Vests. You don’t really need to pack a vest, but if you have room in your suitcase, you’re taking a longer trip, and just want another outerwear option, this is my next pick. I tend to wear vests more when I’m by the coast on a fall trip, paired with a fisherman’s knit sweater, and they work really well to add a layer of visual interest and warmth.
Socks
Yes, I’m making a dedicated section for socks 😂 Because guys, once I figured out my sock situation for fall trips (and honestly, winter trips, too), packing got a lot easier.
The answer is merino wool socks.
I know I’ve talked a lot about the benefits of merino wool layers already, so I won’t get into that, but the same features apply to socks. I now own several pairs, and they all always come with me on fall trips. I have them in hiking socks to wear with hiking boots and fall boots, plus regular socks to wear with sneakers, and they can be worn at least twice, which saves you space in your suitcase (and also keeps your shoes from getting super stinky really fast). They also prevent your feet from getting over-heated.
My Favorite Merino Wool Socks For A Fall Trip:
🍁 Bombas Merino Wool Quarter Socks. This four-pack is really perfect for one fall trip, and these are what I’ll wear with hiking boots or fall boots. They also make a calf-height sock, if you prefer that. I got these as a gift, and they honestly kind of blew me away. They’re so cushiony and comfortable – I immediately ordered more.
🍁 Bombas No-Show Socks. Same as above, but in a no-show version for sneakers. I know the style is to wear higher socks with sneakers now, but I’m a millennial and really struggling with that 😂 So I still wear no-shows with sneakers. If you prefer higher socks with sneakers, you could just wear the quarter socks above – they also come in fun, bright colors.
Hiking Clothes & Accessories
One of the best ways to see fall foliage in New England is by taking a hike. If you’re planning to hit the trails on your trip, here are some of my favorite things that have beat out alternative options over the years. However, if you’re not planning any hikes on your trip, you can skip this section.
Hiking Pants. Whether you prefer leggings or outdoor pants, I have two really good suggestions for you. I actually wear both on fall trips, and just mix it up depending on how I feel that day, and what the weather is like. After years of trying different ones, here’s what’s worked best for me in the fall season:
🍁 Eddie Bauer High-Rise Hiking Pants. I love these because they’re actually high-rise, and stay put without rolling down. They’re water-resistant, which is great if it rains, and they’re also easy to move in. Just really love these a lot. I have short legs, and ordered the petite size, which worked really well for me.
🍁 Eddie Bauer High-Rise Trail Leggings. These are the winter trail version, which I actually really like for fall trips, and they’ve never felt too warm (although, they also work in the winter, too!). These are stay put, down’t roll down, and offer a lot of durable comfort when moving on a hike or trail.
Hiking Tops. I’ve already mentioned that I tend to wear merino wool base tops, with a flannel layered over it on hikes. That’s just my personal favorite combination because I feel like it’s comfortable, looks good in photos, and if I’m heading out to a town or lunch after a hike, it looks appropriate to wear out once I leave the trail.
That said, if you prefer a typical activewear top for hikes, I would go with whatever you feel most comfortable in!
Hiking Poles. As I’ve gotten older, I’ve found that these are crucial for the descent portion of a hike to help protect my knees. Plus, they’ve just helpful to have for any point on the trail, too. I have these inexpensive ones from Amazon, and they work very well. However, if you’re a serious hiker, you likely already have some that are better.
Sling or Backpack. Depending on how many trails you plan to do, and how long they are, you’ll need some kind of bag to carry your essentials in. Any back pack will work if you need a full-size one. But I do have some recommendations on a smaller bag for shorter trails after years of testing out various ones.
🍁 Eddie Bauer Sling Bag. This is such a great size that you can wear crossbody, and also, it has a water bottle holder (which is a dealbreaker for me, because that’s generally the main reason I carry a bag on trails 😂). This is a great option if you don’t need a full backpack, but want something to carry some basics.
🍁 Beis Sport Sling. This is even smaller, and perfect for short trails where all you need is a water bottle, your keys, phone, and wallet. In addition to those things, it will also fit a few more very small things like lip balms. But it’s very small, which is why it’s great. The fact that it’s this compact and has a slot for a water bottle is amazing, which is why I love it so much. This is what I bring on shorter trails where I still need to carry stuff, but don’t need a lot. I honestly use this a ton on fall trips (but also, year-round).
Accessories
Sunglasses. Sometimes people forget these, but you’ll likely need them. Weather varies between gloomy and rain, and bright and sunny. You’ll be glad you packed them!
Hats, Gloves & Scarves. You’ll be happy to have these if you’re planning to head up to a mountain summit, or hike a high peak. The weather is always colder up there, and on years where I’ve forgotten these, I’ve really missed them. I would just pack one of each, and that will be plenty.
Purse. You’ll want one for days where you’re just exploring towns and such. This is also very dependent on personal preference, but my favorite of all time is:
🍁 This crossbody purse. I’ve tried so many purses over the years, and this is the one I now use exclusively – and have been for about three years now. I bought a few different colors to rotate out every season, and I never miss having a different style. I think it’s perfect because it’s small enough to not feel overwhelming, and forced me to carry only things I actually need. But it’s also large enough to have room for a few extras like bandages for blisters, lip balms, medications, sunglasses, etc. It all fits. The front pocket is perfect for your phone and/or keys, too.
The only downside to this purse is that the strap it comes with wears more like a sling bag, and not a true crossbody. You have to purchase a separate, longer strap, which is kind of annoying. But, I love it so much that I was willing to do that, and I get either this thin strap, or this wide strap.
I’m certainly not suggesting that you absolutely need a new purse for this trip – whatever you have that you already use and love will be fine. I always just like to share this one because everyone I’ve recommended it to now also swears by it. My mom only uses this purse now, too.
Road Trip Essentials
Water Bottle. This can also be used for hiking, and it’s an essential on any trip I take. I really like these from Swell because they fit into most water bottle slots in backpacks and sling bags, and are really durable. They also fit into any car cup holder, including the ones on your door.
Car Organizer. Not everyone will need or want this, but I did want to mention it. If you’re doing a longer road trip through New England, buying one of these on Amazon has honestly been really helpful for me. I end up buying a lot of driving snacks, or packing my own tea to make/sip on at hotels, or collecting other random things like trail maps and such on these kinds of trips. Having one place to put it all in my car, instead of using random shopping bags, is the best method I’d tried. It also folds of pretty compact, so it can fit inside a suitcase if you’re flying into the area. However, if this isn’t something you’re immediately like, “yes, I need this,” then I would skip it.
Cameras, Phone & Photography Gear
Camera. Whether it’s your phone or an actual camera, you’ll just need to have one for your trip to capture all the gorgeous fall foliage. This is a wildly personal preference, so I’m going to recommend a specific one. But, I do get asked about my own camera a lot, which is the FujiFilm X-T30, and they don’t even make it anymore, but still make the X-T30 III version, which is pretty much the same (probably better). I also use the Tamron 17-70mm f/2.8 lens, which snaps awesome quality photos.
Phone Cover. You likely already have one, but if you don’t, I would highly recommend once for this trip. Especially if you plan to use your phone as your primary camera. Most people are pretty active on fall foliage trips, whether you’re out on trails, exploring waterfalls, or walking around towns, it’s so easy to get distracted by foliage and drop your phone. Just get a case for the peace of mind if you don’t have one.
Phone strap. I don’t have one of these, but honestly, I’m *this close* to getting this retractable phone strap for this year’s fall trip because I almost drop my phone on every fall trip I take – I’m always whipping it out fast on a hike or while in the car to capture something, and fumble quite a bit. Or worry I’ll drop it at overlooks. I don’t have this yet, so can’t speak to the quality, but I wanted to mention it because for a trip like this, I feel like it will be very handy.
Packing For Cities: Boston & Portland
I start my fall road trip itineraries in Boston, and I know many of my readers like to head up to Portland during fall trips, too. So, I wanted to have a separate section that talks about packing for the bigger cities.
The first thing I want to stress is, you don’t need to pack a lot of extra stuff just for Boston or Portland. They’re still both pretty casual cities, and you don’t really see people dressed up a lot. The exception would be a nice dinner out. But even then, you can still wear jeans, a nice top, and fall boots. Basically, I wouldn’t walk into a nice restaurant in Boston or Portland in hiking gear 😊
For cities, I do tend to dress a little differently, but not drastically different from the rest of my road trip destinations. I still mostly wear jeans and sneakers, but will usually throw on a baseball hat, and maybe pack my trench coat. That’s it, really.
For example, this is usually what I look like while exploring Boston or Portland in the fall season:
Things You DON’T Need To Pack For A Fall Trip
→ Unless you’re planning a more upscale dinner out, you can skip the nice outfits. I do occasionally wear a dress/skirt on a fall trip if the weather allows it, but most of the time, these are the outfits in my suitcase that go unworn on fall road trips. Even when spending a few days in Boston at the end of my road trip. If you’re planning to eat out at a nicer restaurant during your trip, pack one nice outfit, and rewear it if space in your suitcase is limited.
→ Heels in any form. Even fall boots. Because these take up a lot of space in your suitcase, skip them entirely. For their size, they’re just not worth bringing if you’ll only wear them once out to dinner. As mentioned, I’d focus on a pair of flat or low, chunk-heeled fall boots that you can wear while walking around, as well as out to dinner. Do this, and thank me later 😂
→ Tons of make-up, even if you wear a full face every day. If you like to do a full face of make-up every day, go for it. Just don’t overpack lots of different options, and stick to one color palette. If you’re on the fence about how much make-up you want to bring, err on the side of keeping it simple. I don’t personally wear a lot of make-up anymore, but back when I did, I used to always overpack, and only wore about half of what I brought. If anything, just pack a small neutral eyeshadow palette, and a couple of lipstick options. You likely won’t go all-out every day because you’ll be driving in the car, hiking, on nature trails, etc.
→ A huge winter coat. You’ll just be too hot. Stick to light or medium weight fall coats/jackets.
→ An umbrella. As mentioned, if you have a good, waterproof rain jacket, you shouldn’t need an umbrella. It’s uncomfortable to carry when hiking and out on trails, and sometimes the wind make it really impractical. If you have one that’s small enough and you feel more comfortable having it to walk around towns, you can certainly pack it. But you’ll also want to check with hotels you’re staying at, as nicer ones will also allow guests to use their umbrellas. For how often you’ll actually use it, I’ve never found it to be worth the space it takes up.
More New England Packing Tips
→ Check the weather forecast a couple days before you leave for the areas you plan to visit. Weather can vary a lot between places like Boston, versus the White Mountains in New Hampshire, so you’ll want to check each destination you plan to visit. If you’re taking a longer road trip, it may be hard to rely on the forecast for the middle part of your trip if you check right before leaving, as it can change a day or two before. But either way, it should give you a general idea of what to pack.
→ I know I mentioned that is can sometimes snow in the fall season, but this is generally rare. It’s most common up in the norther regions and mountains, but in all my years of traveling, I’ve experienced it maybe twice. And it won’t feel like winter for too long, which is why I don’t suggest bringing any winter gear. On the rare chance that you do get a snowfall, it usually doesn’t stick around for too long in October, and you won’t experience cold, winter weather for more than a half day.
→ If you’re flying in and renting a car: Once you arrive in your first destination, I would put some thing in the back seat of your car right away, including:
- Your rain jacket and extra jacket. That way, if it’s raining, or chilly warm, you have easy access to it.
- Hats, gloves, and scarves. You won’t always need these, but you’ll definitely want to grab them before heading up mountains or higher elevations. These are things you’ll just also want quick access to whenever you are.
- Extra tote bags. These are handy to bring if you have the room in your suitcase for when you buy souvenirs. However, you can also buy these while on your trip if you want.
- Your water bottle, hiking bag, and hiking boots/hiking accessories. I can’t tell you how many times I’ve arrived at a trailhead to realize I left my hiking boots at my hotel. This happens when I do a trail later in the day after exploring another destination first. It’s just a good idea to always have them in your car if there’s a chance you may forget.
This is also why I love having the car organizer for these types of trips. I can keep all this stuff in one place in my back seat, and quickly grab things, add things, and have it all organized.
More Of My Fall Posts You May Enjoy:
- My Ultimate 10-Day New England Fall Foliage Road Trip Itinerary
- My Done-For-You Fall Road Trip Itineraries: Premium Itineraries That Make Decisions For You
- Best Time To Visit New England For Fall Foliage
- Fall Color In New England: Where To See The Best Foliage
That’s A Wrap On What To Pack For A Fall Trip In New England
This post boils down years of experience into these key things you’ll want to pack for your New England fall trip. I hope it’s helped you hone in what you actually need for your adventure, and what you can confidently leave at home. Remember, think in layers, merino wool is your friend, keep your footwear comfortable, plan for rain, and don’t forget that camera. Happy packing!
