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What to Pack for a New England Fall Road Trip: My Ultimate Checklist (Plus how to pack in a carry on!)

By Helene Sula

Planning a New England fall road trip is a bucket-list experience. Picture this: winding backroads framed by vibrant fall foliage, charming small towns with pumpkin-lined streets, and crisp autumn air that smells like apple cider. But here’s what most people don’t realize: packing for a fall road trip in New England isn’t as straightforward as you might think.

After exploring Vermont, New Hampshire, Maine, and Massachusetts every autumn for years, I’ve learned what’s essential to pack (and what you can leave at home). Whether you're planning a weekend getaway or a two-week New England foliage road trip, this guide has you covered.

Here’s exactly what to pack for a New England fall road trip—so you can focus on chasing peak fall colors and sipping cider.

Exact Turtleneck Sweater Dress linked here.

Before we begin… I have DOZENS of guide to New England! All found here!

Why Packing Right for New England in Fall Matters

New England autumn weather is famously unpredictable. Mornings can be sunny and warm; afternoons chilly and misty; evenings downright cold. And rain? Almost guaranteed at least once on your trip. That’s why your New England fall packing list should focus on:

  • Layers for changing temperatures
  • Waterproof essentials for rainy days
  • Comfortable, practical footwear
  • Cozy extras to embrace the fall vibes
  • Road trip and hiking essentials

Let’s dive into the complete list.

A quick note! I'm a big believer in packing light. I pack EVERYTHING into a carry on. And I've written many guides on packing. It can feel overwhelming but having a few key layers is perfect, then add some accessories! This is the bag I use for travel.

🍂 What to Pack for a New England Fall Road Trip

I promise, you can look exceptionally cute while also packing light for New England for Fall! I'm going to show you exactly what I bring and also give you links to where you can find similar!

Let's go over what I think you must bring:

If you have these you honestly you can really mix and match so well! You can always pair your long sleeve top with your skirt or your sweater with your leggings and vice versa.

I'm going to give you my exact pieces as well as multiple places you can buy these items.

Must Have Items for New England in the Fall

Leggings

Leggings // Hiking Boots // Top // Socks

First up leggings. This is my go-to and something I never travel without. I've done whole posts on leggings and these remain my favorites. Leggings are great, especially for fall in New England, because you can wear them with everything. I like:

You can see my guide to the best leggings for travel here.

Long sleeve tops

Fall in New England is all about layering, and a long sleeve top is the unsung hero of your travel wardrobe. You’ll want something that’s breathable enough to wear during a sunny afternoon stroll through town, but warm enough to layer under a jacket for an early morning hike. Bonus points if it’s a moisture-wicking fabric—because yes, even in autumn, hiking uphill will make you sweat.

Jeans

Jeans are a fall classic for a reason. They’re versatile, durable, and perfect for those casual days spent exploring small towns or grabbing a bite at a roadside diner. I recommend stretchy or straight-leg jeans for comfort, especially if you're sitting for long drives. And don't worry—they pair perfectly with boots and your favorite fall flannel.

These jeans are extremely flattering and a good price point. These “curve love” jeans from Abercrombie are my absolute favorites.

Sweater

If you don’t pack at least one cozy sweater, did you even go to New England in the fall?! I'm a big fan of a cream sweater but also love a good fall sweater with details! A chunky knit or fleece pullover is ideal for layering over your long sleeve tops, and they’ll keep you warm when the temps start to dip—especially in the mountains or near the coast where it gets breezy fast.

Boots

I typically bring one or two pairs: one for hiking and one for feeling cute with leggings and/or skirts! These hiking boots are ones I've talked about for YEARS. I wore them to walk hundreds of miles!

Comfortable, waterproof boots are a must. You’ll likely be walking on trails, crunchy leaves, maybe even some muddy ground depending on the weather. I recommend ankle boots with good tread or waterproof hiking boots. These are perfect for both city strolling and spontaneous scenic overlooks. Trust me—you don’t want to be slipping around in sneakers.

I also like some cute knee high boots to wear to get apple cider donuts!

Hat// Beanie

A hat might seem like a cute accessory (and it is!), but it also serves a purpose. It keeps your head warm during chilly mornings and helps block the wind. I usually pack a wool beanie or a felt wide-brim hat—both practical and very fall-photo-op-friendly. I think a good chunky beanie can just complete the outfit!

Socks

This may sound dramatic, but good socks can make or break your day. I always pack a few pairs of wool or cushioned hiking socks. They keep your feet warm, dry, and blister-free—whether you're trekking up a mountain trail or just wandering through a pumpkin patch. Don’t skimp on these!

Skirt

A skirt in the fall? Absolutely. Pair it with tights and boots and you’ve got yourself a cozy-but-cute outfit for town exploring an apple orchard or a nice dinner out. I usually bring a midi skirt that can be dressed up or down, and it takes up barely any room in your bag.

Tights

These are a game changer. For New England fall I like to pack regular tights, but if it gets chilly there are fleece lined options! Fleece-lined tights let you wear dresses and skirts without freezing your legs off. They’re also great for layering under jeans or leggings if the temps really drop. I’ve worn these under a raincoat on a damp, 40-degree day in Vermont and stayed totally warm and dry.

I prefer these tights overall as they come in classic black or a variety of colors!

Jacket (Rain Jacket)

Fall in New England is known for its color… and its weather mood swings. A packable, waterproof rain jacket is essential. Even if the forecast looks clear, don’t be fooled—a sudden drizzle can hit at any moment, especially in the mountains. I recommend a lightweight shell you can layer under, or a 3-in-1 jacket if you want extra insulation.

I don't even want to begin to talk about how long my husband researched this rain jacket. But it involved… spreadsheets.

I also love this jacket– an investment but you'll have it for life!

Flannel Shirt

Can you even call it a New England fall trip if you don’t pack a flannel? This is the ultimate autumn layering piece. Flannel shirts are warm but breathable, perfect for tossing over a long sleeve tee during the day or under a jacket at night. They also scream fall foliage fashion—and yes, they look adorable in photos next to covered bridges and maple trees. Bonus: they double as a light jacket if the weather is mild. I usually bring at least one in a classic plaid, and I always end up wearing it more than I expected.

I love a flannel because you can easily tie it around your waist and add a pop of color!

How to Pack For a New England Fall Trip

1. Layered Clothing for New England’s Fall Weather

Wondering what to wear in New England in fall? The answer: LAYERS.

  • Long-sleeve tops: Breathable, moisture-wicking fabrics are ideal.
  • Fleece pullover or cozy sweater: A must-have for those cooler days.
  • Rain jacket: Choose something lightweight yet fully waterproof.
  • Insulated jacket or puffer: Especially useful in late October or northern areas like the White Mountains.
  • Thermal leggings or long underwear: Optional, but great for cold mornings.
  • Comfortable jeans or hiking pants

Don’t forget the accessories!

  • Warm hat (like a beanie or wool cap)
  • Gloves or mittens
  • A scarf – bonus points if it’s a cozy plaid for those fall photos!

2. Waterproof and Comfortable Footwear

You’ll be walking through quaint towns, hiking up scenic overlooks, and crunching through leaves. Your shoes need to handle it all.

  • Waterproof hiking boots or sturdy walking shoes
  • Casual slip-ons for town strolls
  • Wool socks (warm, moisture-wicking, and cozy)

Tip: Avoid new shoes—blisters and road trips don’t mix.

3. Road Trip Essentials

Don’t hit the road without these must-haves:

  • Reusable water bottle (stay hydrated!)
  • Snacks: Apples, granola bars, and locally made treats.
  • Phone mount or holder for navigation.
  • Google Maps downloaded offline – trust me, cell service in Vermont’s mountains can disappear.
  • Paper map as backup.
  • Cooler for local goodies (like cider and cheese!).
  • Reusable shopping bags (for farmers' markets and roadside stands).
  • Portable phone charger or power bank.
  • Flashlight or headlamp.

4. Fall Photography & Tech Gear

New England in autumn is pure magic for photographers.

  • DSLR or mirrorless camera (optional, but worth it).
  • Smartphone with a good camera.
  • Extra memory cards and batteries (cold temps = faster battery drain).
  • Portable charger.
  • Tripod (especially for waterfall or sunrise shots).

5. Rainy Day Essentials

Rain is part of the charm… as long as you're prepared.

  • Packable rain jacket (I can’t emphasize this enough!).
  • Small travel umbrella.
  • Dry bag or ziplocks for electronics.

6. Cozy Extras for Fall Vibes

These aren’t essential, but they’ll make your fall foliage adventure feel extra cozy:

See my full Amazon packing guide here!

🏞️ Optional Items for Hiking & Outdoor Adventures

I'm a hiker so I'm a big fan of making sure I have what I need to go walk through the foliage. One thing I love is the insect sheild clothing (yes, there are ticks in the North East). Planning some hikes in places like the Kancamagus Highway or Franconia Notch?

I pack everything in this!

🏕️ Are You Camping or Staying in Cabins?

If your New England fall road trip includes camping:

  • Sleeping bag rated for cold nights.
  • Sleeping pad or air mattress.
  • Camp stove or portable cooking gear.
  • Firewood (or buy locally).
  • Extra dry clothes in case of rain.

📋 Your Printable New England Fall Road Trip Packing Checklist

Want an easy-to-use checklist? I’ve created a FREE printable version of this packing list! Drop your email below and I’ll send you my full packing guide—plus my New England fall road trip itinerary and map.

(Insert ConvertKit email signup form here.)

🎃 Bonus Tips for Packing for Fall in New England

  • Expect temperature swings. Bring items for both warm afternoons and freezing mornings.
  • Bring cash. Many small shops and farms don’t take cards.
  • Leave space in your suitcase. Trust me—you’ll want to bring home maple syrup, local crafts, and probably a new flannel.

Why Trust My Packing Advice?

I’ve taken a New England fall foliage road trip every year for nearly a decade. From the mountains of Vermont to the coastal towns of Maine, I’ve experienced sunshine, rain, snow flurries—and everything in between. This list isn’t just a Pinterest-friendly wishlist; it’s based on real-life experience.

Want my exact route and insider tips?
Don’t miss my full guide: The Perfect New England Fall Road Trip Itinerary for Leaf Peeping.

See all the guides here:

The Perfect New England Fall Road Trip Itinerary for Leaf Peeping

New England Fall Foliage Prediction Map

Best Places for Fall in Vermont

Best Places for Fall in New Hampshire

Best Places for Fall in Connecticut

Guide to Salem, MA

Hocus Pocus Filming Locations

Ultimate One Week Fall Foliage Itinerary

20 Best Places for Fall Foliage in New England

Best Farms, Towns, and Festivals in New England

Best Places for Europe in the Fall

Fall Instagram Captions and Photo Ideas

New England in the fall is one of the most beautiful places on earth. With the right gear packed and your layers ready, you’ll be able to soak in every moment—from the golden leaves to the pumpkin-spiced everything.

Happy road tripping and leaf peeping! 🍁

MEET THE AUTHOR

Helene Sula

I believe that one trip can change your life. It did for me. I'm a self proclaimed home body that quit her job, moved abroad, and more often than not, lives out of a carry-on bag. If I'm not traveling, I'm most likely re-reading Harry Potter or watching "Midnight in Paris" while snuggling my dogs. I'm a digital marketing expert who turned my love of travel into a full-time career. And I help others do it too.

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