Last year I finally did it! I took the ultimate fall foliage road trip through New England. Think Vermont covered bridges, apple cider donuts, Salem in October, and mountains glowing red and gold.
Since fall is my favorite time of year, I went all in on the autumn aesthetic, and yes, I carefully planned my outfits to match the vibe. Sue me.
If you’re searching for New England fall outfits or wondering what to wear in New England in the fall, this guide is for you. These are the exact fall inspired outfits I wore (and what my friends wore, too) while exploring Vermont, New Hampshire, and Massachusetts.
Why Your Fall Outfits Matter in New England
New England autumn weather is unpredictable. Some mornings started out in the 40s with fog, afternoons warmed up to the 70s, and evenings dropped again once the sun set. Add in surprise rain showers and you’ll quickly see why layering is everything.
Thankfully, as a gal who lives in San Francisco aka the city of layers, I knew how to approach this.
I wanted outfits that looked great in photos but also kept me comfortable, whether I was hiking, canoeing, or wandering through a corn maze.
My Real New England Fall Outfits I Actually Wore As A Size 14
I’m 5’5″ and wear a size 12 or 14 in everything, by the way!
Covered Bridge Outfit – New Hampshire
Nothing feels more New England than a covered bridge in October. I think it’s the law that you have to stop and take a photo of one when you are on a New England fall road trip
For this look, I wore an orange plaid shacket, black pants, boots, and a beanie. Cozy and practical since we started our Kancamagus Highway drive at dawn, and it gave me that lumberjack-but-cute vibe for a day spent exploring small towns and pulling over for every scenic bridge we could find.
Canoeing on a Vermont Lake
We stayed at a historic farmhouse B&B in Vermont that had canoes for guests, and I couldn’t resist paddling out at sunset. For this, I wore my Sézane red sweater with black Anthropologie pants.
The bold color popped beautifully against the water and foliage, and it was warm enough for sitting out on the lake in October.
Downtown Stowe Coffee Run
Stowe in the fall is straight out of a postcard. While wandering downtown with a maple latte in hand, I wore a Pink Lily puffer vest (with pockets!) layered over a Kiel James Patrick fall sweater.
This combo was equal parts cozy and festive, perfect for strolling past general stores and pumpkin displays.
PS read my full Kiel James Patrick review here to see if it’s worth shopping or not.
Stowe Street Style (Friend’s Look)
My friend leaned into comfy-cute New England vibes with black pants, a black-and-white fuzzy jacket with arrows, a pom beanie, and cute ankle boots.
A simple outfit that worked for everything from coffee runs to leaf-peeping.
Woodstock Stroll
Woodstock, Vermont is one of the prettiest towns in fall. I wore my leaf-print sweater, black mini skirt from Amazon, tights, and ankle boots while walking pumpkin-lined fences. This look felt playful and whimsical, basically fall embodied.
Canoeing (Friend’s Look)
My friend kept it casual with jeans, a green jacket, and booties while we were canoeing. A great example of a fall inspired outfit that’s functional for the outdoors but still looks polished for photos.
Kancamagus Highway Outfit (Friend’s Look)
For a day on “The Kanc,” my friend wore a leaf-print sweater, we twinned on these (but she found an Amazon version that was a fraction of the cost), jeans, and a long rust-brown coat. Against the backdrop of barns and fiery foliage, it felt like the ultimate classic New England fall look.
You could also swap the cardigan for a trench coat and get a similar vibe!
Matching Fall Sweaters in Stowe
One of my favorite memories: my friend and I both wore Kiel James Patrick fall sweaters while leaf-peeping in Stowe. I paired mine with my brown Anthropologie pants, while she styled hers with jeans.
These sweaters are basically made for New England and instantly give you that cozy, timeless autumn vibe. You don’t even need fun accessories when wearing these iconic sweaters, they do all the heavy lifting for you.
Corn Maze in Stowe
During the day it warmed up, so I took off my sweater and styled it across my shoulders in a preppy way. I wore a white bodysuit from Pink Lily under and found myself styling this top a lot during our trip as a basic.
I wore brown pants, a white long sleeve top, boots, and sunglasses while running around a corn maze. Comfortable but still cute for those golden hour photos.
Witchy Vibes in Salem
You can’t travel to Salem in October without leaning into the witchy aesthetic. I wore a black tulle skirt, black sweater, black boots, and a wide-brim hat.
It felt whimsical and fun, but also perfectly on-theme for exploring haunted houses, Halloween festivals and all the Hocus Pocus filming spots.
Marblehead Graveyard (Hocus Pocus Filming Spot)
We stopped in Marblehead, Massachusetts to visit one of the Hocus Pocus filming locations. My friend wore a pumpkin-print fall sweater (she had the best tops on this trip!), brown mini skirt, tights, and boots.
It was festive, photogenic, and a great nod to Halloween without being a costume. I re-wore my Salem black tulle skirt outfit here, which blended right into the spooky vibes.
New England Fall Packing List
Wondering what to pack for New England in the fall? Here’s the exact checklist I recommend based on my trip to dress like a New Englander leaf peeping.
This mix of cozy layers, practical shoes, and fun seasonal pieces will cover you from apple orchards to spooky Salem nights. I brought almost everything on this list to my fall trip.
Clothing Essentials
- Lightweight long sleeve tops (great for layering)
- Cozy sweaters (chunky knits, turtlenecks, fleece pullovers)
- Festive sweaters (pumpkin, leaf, or plaid prints for that fall vibe)
- Jeans (straight-leg or cropped work well)
- Leggings (for hiking or lounging)
- Skirts + fleece-lined tights (cute but warm)
- Dresses (sweater dresses are easy one-and-done outfits)
Outerwear
- Plaid shacket or flannel (perfect for covered bridges and orchards)
- Trench coat or wool coat (classic preppy New England style)
- Puffer vest (lightweight but warm)
- Packable rain jacket (yes, it will rain at least once)
Shoes
- Waterproof ankle boots
- Comfortable walking boots (for leaf-peeping hikes)
- Casual sneakers or loafers
- Knee-high boots (for dressier dinners or nights out)
Accessories
- Beanies (wool or chunky knit)
- Plaid scarf or blanket scarf
- Leather belt (adds polish to oversized sweaters)
- Crossbody bag (hands-free for cider sipping + pumpkin picking)
- Gloves (if traveling late October into November)
Optional but Fun
- A wide-brim hat (especially in Salem for witchy vibes)
- Statement sweater (pumpkins, leaves, or fair isle)
- Tulle or flowy skirt (makes photos extra whimsical)
Tips For Styling Fall Outfits in New England
- Layers are everything: Start with a tee or base layer, add a sweater, then a jacket or vest when building early fall outfits, as the weather swings day by day.
- Bring waterproof boots: Muddy orchards, wet leaves, and surprise rain showers are common.
- Play with textures: Flannel, wool, suede, and tulle all look amazing against fall foliage are great for classic preppy fall outfits.
- Lean into seasonal themes: Pumpkin-print sweaters and leaf motifs are not too much, in New England, they’re just right.
- Accessorize smartly: Beanies, scarves, and crossbody bags make outfits feel complete while keeping you warm and hands-free.
My Takeaway: Dressing for New England Fall Adventures
New England in the fall is pure magic, and dressing for it made me feel like I was stepping into a Hallmark movie. These New England outfits weren’t just cute for photos they were practical for road-tripping, hiking, and wandering through cozy towns.
Plus, I had so much fun leaning into a slightly more preppy style than I normally wear for this trip while still making it very much me.
If you’re heading to New England in the fall, I recommend packing at least one festive sweater (pumpkins, leaves, or plaid), one cozy cream or red knit, and a pair of waterproof boots.
Those pieces will carry you through just about any adventure, from canoeing on a Vermont lake to sipping cider in Stowe.
Trust me, you’ll come home with hundreds of photos and an even bigger love for fall fashion.
