How to Pack for a Fall Weekend Getaway

Caitlin Houston
6 min readOct 12, 2023

Wondering how to pack for a fall weekend getaway?

Fall is a busy season, with each weekend holding plans for family activities or projects around the house. Amidst all the chaos, I love being able to forget it all to pack up for a fall weekend getaway. Every time I travel during autumn in New England, I reference this post written in 2018. Here is how to pack for a weekend away during the fall.

Packing a Bag

**Original post written 2018 — minor changes are made every year, including up-to-date fall fashion, affiliate links, and more tips for packing for a fall trip.**

We celebrated our ninth wedding anniversary in Falmouth, Cape Cod and Nantucket, two beautiful locations in New England on our bucket list. I prepared for this trip for a week, laying outfits out on the bed, and then finally packing everything the morning of our trip. I’m excited to share with you what to pack for a fall weekend getaway.

Packing for a fall trip in Lo and Sons Catalina Bag woman wearing pink blazer with dark jeans

Thank you Lo and Sons for the Catalina Bag. This bag fits EVERYTHING you need for a weekend trip!

LAYERS are a Travel Essential during the Fall

The temperatures during fall in New England are brisk and inconsistent. Checking the weather forecast before a big trip is necessary, but I like to be prepared for all weather patterns. Instead of bringing a variety of outfits, layering is the best way to dress for the fall. Layers are crucial during autumn when the mornings are cool and the afternoons are warm.

JCrew sweater over a dress, knee high boot socks, and riding boots

A sweater blazer, puffer vest, layering shirt, cape scarf, jean jacket or city coat are all ideal items to bring along on a trip during the fall. A sherpa or fleece pullover, leggings or tights, and a tunic sweater are easy to layer as well. Some of my favorite fall wardrobe must haves in New England: fisherman cardigan, fisherman tunic, and Dudley Stephens fleeces. This year I picked up an open sweater cardigan that feels like a coat (coatigans are always popular layering pieces for the fall).

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See my Mini Fall Wardrobe Capsule here for outfit inspo!

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Easy Layered Outfits for Fall

There are many options for layered outfits for fall. One example is a long sleeve top under a vest paired with a mini skirt, tights, and riding boots. Another variation of this outfit would be a cardigan over a tank paired with a silk maxi skirt and flats.

JCrew puffer vest, sweater, plaid skirt, tights, knee high boot socks, and riding boots

Outfit Above: Vest // Sweater // Skirt (similar) (similar) // Tights // Boot Socks // Boots // Vintage Gucci

printed cardigan white button down green corduroy skirt knee high boots fall fashion caitlin houston

When considering what to pack for a fall vacation, always leave room for shoes!

I love fall footwear. Riding boots, loafers, white sneakers and booties came along with me on our trip. I also bring camp socks, a pair of tights, and knee high boot socks to layer under my shoes. One big regret: leaving my LL Bean Duck Boots at home, especially since it was very cold watching the sun come up on Nantucket.

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Winter Hat, Gloves, Puffer Vest, Warm Shoes - Nantucket Sunrise Outfit

Fall Travel Outfits Over the Years

Fall Maternity Photo in Field
Shopping in West Hartford
Woman with red and black jcrew flannel and white puffer vest
Woman in Grayson Button up sitting on ramp to Red Barn in Vermont
Gray Cable Knit Sweater
brown sweater cardigan with turtleneck corduroy skirt and riding boots
fall travel outfit cashmere set with long cardigan caitlin houston

Don’t forget to Pay attention to the weather

Going on a date night during the fall can be tricky. The temperatures may drop drastically while you’re eating dinner. If you are walking from place to place at night, you want to look cute while staying warm. I almost left some important accessories reserved for winter at home.

If you’re traveling around New England during the fall, pack a pair of gloves, a hat and a scarf! A pair of fingerless mittens, fur infinity scarf, and winter hats are cute accessories for a cool evening. This is a great brand for knitwear and this is a great brand for fall hats.

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What to Pack for a Fall Getaway - Peacoat, winter hat, leggings

The Ultimate Packing List for a Fall Weekend Trip

  • Weekender Bag
  • 1 pair of comfortable wear all-day-long shoes (sneakers, rain boots, bean boots, etc)
  • 1 pair of dressy boots or heels
  • 1 pair of comfortable multi-use pants (jeans or leggings)
  • 1–2 tops — casual and fancy (for dinner)
  • 1–2 dinner outfits (skirt + sweater, dress, jeans + top)
  • 2–3 pairs of undergarments
  • 2 pairs of socks
  • 1–2 pairs of pajamas
  • 1 jacket (if casual, also pack a more formal jacket for evening)

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Check out more fall style during my autumn weekend trips:

Girl’s Weekend in Newburyport, A Fall Family Vacation to Martha’s Vineyard, A Romantic Fall Getaway to Cape Cod, A Guide to Exploring Vermont in the Fall with Joules

This post contains affiliate links — if you make a purchase using my links I may make a small commission. As always, Caitlin Houston Blog greatly appreciates your support!



Caitlin Houston

Caitlin Houston is a Mom of three and creator of Connecticut based life + style site Caitlin Houston Blog.