What to Pack for a Fall Trip to New England

Each year I like to go on a big vacation to someplace fun. Last year it was Disney World in Orlando Florida. This year we did a road trip through New England. New England is comprised of Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island. We went to all of these states except for Vermont. Over the course of 7 days, we traveled 1,000 miles all the way from Pennsylvania to Maine.
We were in Massachusetts for a majority of our trip visiting Plymouth, Boston, and Salem. Then we drove up to Portland, Maine to enjoy the beer and lobster. Our last stop was Portsmouth, New Hampshire to spend time with a childhood friend. Now all of these places were went were coastal towns that were right near a harbor. This means that the temperature dropped and that it would be very windy – I was not prepared for that.ย Each place had a different climate. Plymouth was nice and warm, Salem was raining and freezing, and Portland was very windy. All of these different types of weather made packing for this trip a challenge. I had to be ready for everything.
This is everything that I packed for our trip as well as some items that I wish I would’ve brought with me!


Since there were so many different types of weather that I would be enduring, I had to bring a lot of tops, and cute tops too that I could make outfits out of. I packed with me a white striped long sleeve shirt, a cute sweater, two sweatshirts, a long grey cardigan, a couple basic t-shirts, and tank tops. Also, I had to pack jackets so I brought an olive green jacket, a lightweight zip-up jacket, and a heavy duty winter coat. I’m so glad I had that winter coat too. I wore it a lot in Salem and Boston where the temps dropped to 50 degrees.


Pants were the easy part because I really only wear a few pairs of pants as it is I packed a pair of dark wash and light wash skinny jeans, black leggings, and two pairs of pajama pants. I also included a skirt but I didn’t end up wearing it because it was too cold. but I had it just in case.


Shoes were the most important thing I had to think about because our trip involved a lot of walking. Each day I had planned out a historical walking tour or a food tour so we had to have comfortable shoes. I packed 1 pair of comfy sneakers, UGG boots to keep my feet warm, 1 pair of knee-high boots, 1 pair of ankle booties, and 1 pair of rain boots. Actually I never wore the rain boots (I should have) because the one day it rained I forgot to wear them! I wanted to include some cute boots so if we went out to a nice dinner or saw friends, then I would have nice shoes to style with a cute outfit.


The best accessories that I had on this trip was my tote bag. It held EVERYTHING! from direction to our hotels to tickets for the walking tours, I had souvenirs that we bought, water bottles and snacks, and my camera. We had to stop at the car a lot so I could take things out of my bag because it became quite heavy, but I am so glad I brought a huge bag. I am also grateful for my umbrella that kept me dry in Salem, the sunglasses that I wore for the one nice and sunny day in Plymouth, and my scarf that kept me warm in Portland. All of these accessories were very important to have.

Overall I would say that I packed pretty well and had everything that I needed. I do wish that I had brought gloves and a hat to Salem because it was FREEZING, but I was okay as long as I had a cup of hot coffee or hot chocolate in my hand. Also, I over packed a little with all of the warmer weather clothing that I didn’t wear at all. Our road trip was a lot ofย  fun and I loved exploring new places but I am happy to be home and sleeping in my own bed again. I hope to go back to these places sometime soon because I really did have a lot of fun. I would love to see Portland and Boston in the summer!
Have you ever been to New England?


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  1. November 12, 2018 / 8:32 pm

    Great post! Your road trips sound amazing! I seldom travel far without my tote bag – it’s amazing how much you can fit into a bag ๐Ÿ™‚

    • CozyStylist
      November 12, 2018 / 9:08 pm

      My tote bag is like the bag from Mary Poppins haha it fits so much stuff! So glad you liked the post ๐Ÿ™‚

  2. November 12, 2018 / 9:05 pm

    I love how you’ve added actually links to items so that I can look at them. I really dislike it when I’ve seen an item I like but there is no link to be able to purchase it. Great idea! I’d probably buy a lot of these things anyway as it can get quite cold here in England and I’m always after new things to wear so I can stay warm and toasty ๐Ÿ˜Š

    • CozyStylist
      November 12, 2018 / 9:09 pm

      I always link to the item or something very similar to it so that others can buy the items that I’m talking about! Thanks for reading ๐Ÿ™‚

  3. November 12, 2018 / 9:35 pm

    I’ve never been to New England! But everything on your packing list is very practical and stylish! I always end up overpacking so I’ve made a spreadsheet now to make sure I pack exactly what I need haha x



    • CozyStylist
      November 12, 2018 / 10:43 pm

      I should’ve made a spreadsheet haha that sounds like a very smart idea!

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