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What to wear in the Fall in New England?

It’s Fall ya’ll… which means, it’s the kind of weather for cutesy sweaters. And girl do I have some cute ones for you!

But, just because you have to cover up, doesn’t mean you can’t look super stylish!

Whatever you’re planning on doing… pumpkin picking, apple picking, horseback riding, a picnic, or another adventure… here’s what to wear to look totally fashionable and fierce in New England this Fall.

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What to Wear in New England in the Fall

Different New England Looks to Rock This Fall

Fall Fashion

The “Laid Back, Edgy” Look 

Where I wore it:

Fall Edgy

Pumpkin Picking at McQuesten Farm – Litchfield, NH

Fall Edgy Look Book #1 

One day in October, my friend John and I decided it was the perfect Fall day to go pumpkin picking! When we tried to find a cute farm in New Hampshire, lots of options came up, but none that we were totally dazzled by. Then, we went to Pet Smart. Yes, Pet Smart. (not sponsored). 

We were picking up some things for his dog, Rudy and that’s when the cashier overheard us talking about finding a pumpkin patch. She went to school with someone who owned this adorable farm called McQuesten that had not just pumpkin picking but a hayride that takes you to the patch.. but also… popcorn, inflatable slides, and a petting zoo… It was super cute! We just had to go.

What I Wore

I felt a little edgy that day so, I went with my Harley Davidson boots, a matching Harley jacket, and some jeans to pick pumpkins.

WaterFire Festival at Providence, RI

Fall Edgy Look Book #2

I’d heard about the WaterFire festival for some time since moving to New England and so, I decided to go one Saturday in November. Luckily for me and everyone, I went with, it was a special Veteran’s Day celebration. The ceremony was absolutely beautiful. It made all the water and fire theatrics so much more powerful and has resonated with me even years later! Not to mention, they had delicious food vendors and kettle popcorn stands. 

What I Wore

It was a bit chilly out so I decided to go for a bit more of an edgy look with knee-high leather boots paired with a matching black beanie, jacket, and gloves.

Favorite Fall Finds

The “Girly” Look 

Where I wore it:

Girly Finds

Apple Picking at Currier Orchards – Merrimack, NH 

Girly Look Book #1

One day, after doing some shopping, I scored an apple sweater by LOFT. It was super cute and just the inspiration I needed to do the real thing. So, I decided to go to this adorable farm called Currier Orchards which had old-fashioned Radio Flyer wagons and baskets that you could tote around the fields while you picked apples. There were even old, rustic barns around and vintage tractors. That, coupled with the Fall foliage all around, the whole scene was so legit.

What I Wore

I decided to go girlier than the previous apple-picking adventure and instead of going country chic, I opted for a more girly vibe wearing a sun hat with a bow, cream-colored pants, ballet flats, and of course, my apple sweater with a cute flower belt. I felt right in my element!

A Fall Picnic at Madame Sherri Forest – Chesterfield, NH

Girly Look Book #2

This is a place known by pretty much every local in New England.. or at least, New Hampshirians. This spooky forest is known as “Madame Sherri Forest” is the scene for many Fall photoshoots and it’s no wonder why… when the foliage happens, it’s very enchanting. For my birthday, I was surprised with a lovely picnic. 

What I Wore

I decided to wear something a bit more Fall festive with warm tones but still wanted to dress cutesy and feel girly. So, I went for a brown leather jacket, burgundy pants, an off-the-shoulder floral patterned dress, and UGG boots.

A Birthday Dinner at Little Red Riding Hood’s House, Pickity Place – Mason, NH

Girly Look Book #3

You’d be amazed at what you discover when you keep your eyes on the road. That’s how I discovered Pickity Place in Mason, NH… and what a charming and idyllic place it is. It’s nestled in the middle of the woods and the inspiration for “Little Red Riding Hood”. There, they serve pre-fixed meals with herbs they’ve grown in their garden. They change their menu every month and all their food is seasonal. The whole experience is quaint and lovely!

What I Wore

I wore two different looks technically. Naturally, I had to dress like Little Red Riding Hood. And that’s exactly what I did! For this look, I wore a red cape which acted as a cloak with holes to put your arms through, a white turtle neck sweater, and black pants, and black calf-length leather boots.

For my second look, I wore a pink polka dot dress with a thick black belt, black tights, and boots.

The “Country Chic” Look

Where I wore it:

  • Home with an Apple Pie 

Country Chic Finds

Apple Picking at Mack’s Apples – Londonderry, NH

Country Chic Look Book #1 

Apple picking has been a tradition in my family. Craving a fun, Fall adventure in New England, I headed out to Mack’s Apples in Londonderry, NH. It was September… the perfect time of year to pick apples! It was very tasty, they had apple juice samples from different apples. 

What I Wore

I felt a little country chic.. so I went for some overalls. It made me feel like a farm girl… and just like that, I was right in my element. I loved it! Made the experience so much more authentic.

Fall in New Hampshire: Favorite Fall Activities in NH

Have you visited New Hampshire in the Fall? Go apple picking, see the place that inspired Little Red Riding Hood, go on a fall picnic and so much more. Check out my New Hampshire fall itinerary.

Horseback Riding at Lucky 7 Stables – Londonderry, NH

Country Chic Look Book #2

I’ll never forget this riding experience at Lucky 7 Stables! I went for my sister’s birthday and we had such a blast! Our guide, Ernesto, was super friendly and made us laugh so much with his cowboy tunes and Old Western-style voice. He even sang her Happy Birthday! We all had such a great time trotting along the trail, taking in the foliage. It was definitely my favorite riding experience of all time.

What I Wore

To ride horses, I decided to go with a more country look to fit the scene and wore a jean jacket, riding gloves, riding helmet, gingham shirt, jodhpurs, and knee-high leather boots. 

Baking Apple Pie – Home 

Country Chic Look Book #3

Baking apple pie is one of my sister’s favorite things to do. We decided to get cutesy and do a little photoshoot too!

What I Wore

I felt very farm girl so, I wore a cute gingham top and ripped Daisy Dukes.

A Day of Fall Fun at Deep River Farm – Deep River, CT

Country Chic Look Book #4

For a day at Deep River Farm, I picked pumpkins, ate apple cider donuts that I got from their farm stand/market, and walked through the farm to the animals. I even raked hay. I was like a true farm girl.

What I Wore

Fall is the time to be exploring nature and getting in the scenery. Sometimes, it’s not realistic to wear high heels and dresses. For my time at the farm, I decided to do a total 180 and go casual. 

The “Nature Look” 

Where I wore it:

Leaf Peeping at Height of Land – Rangeley, ME

Nature Look Book #1

One of the most popular Fall foliage sights in Maine is Height of Land and for good reason, it’s breathtaking! We pulled up, parked the car, sat on one of the rocks near the overlook, and enjoyed a nice Fall picnic… then, took in the gorgeous views all around.

What I Wore

A black and white checkered flannel long sleeve shirt, green vest, black yoga pants, and black leather boots.

Hiking at Sugarloaf Mountain – Carrabassett Valley, ME

Nature Look Book #2

The scenery at Sugarloaf is beautiful on any given day… But, Fall? Forget about it! It’s absolutely gorgeous. I took a little stroll through the woods on one of the trails and enjoyed some leaf peeping. The colors were intense!

What I Wore:

Wanting a simple look to do some hiking, I went for a white plaid long sleeve shirt tied up, black yoga pants, and black high-heeled tennis shoes. I rolled up the sleeves for a more comfy, casual vibe.  

Biking the Railroad & a Mimosa Brunch at Rail Explorers – Portsmouth, RI

Nature Look Book #3

One of my favorite things about Fall is getting to enjoy the scenery while doing something fun and eating something yummy. For this fun adventure, I went to Portsmouth, RI, and stopped by Rail Explorers where I got the best of both worlds. It’s a fun bike ride that you pedal along the Narragansett Bay followed by a break for some brunch, mimosas, and stunning sights. I love that they have different packages.  

What I Wore:

Not having very many options for a physical activity like biking on a railroad, I decided to keep it casual. I wore a grey zip-up collared jacket, jeans, a white beanie, paired with leather boots.

Rhode Island in the Fall

Looking for other fall activities in New England? Read more about my fun fall discoveries in Rhode Island.


No matter what you decide to do in New England, you’ll be fashionable and fierce for Fall! 

geeves fall illustration

What is your favorite fall look?

Thank you for reading my blog! I hope you enjoyed my Fall looks. Let me know in the comments below which look(s) you’re inspired to try this Fall! I’d love to hear it! 😊

If you enjoyed this blog, I’d love it if you left a comment below. You can also follow me on Twitter and Instagram!

Would you like more of this type of content? Or maybe there’s something else you want me to write about?

If you enjoyed this post, you might also like:

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Fall in New Hampshire: Favorite Fall Activities in NH

Rhode Island in the Fall: Make New Discoveries this Fall

The Ultimate Packing List for Every Type of Traveler

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