We just returned home from a wonderful fall weekend away in the Litchfield Hills here in Connecticut. This is one of our favorite regions to visit in October. This week, I’ll share a full guide with details about where we stayed and places we enjoyed visiting around the county. Today, I wanted to share some great new fall pieces I wore on this trip. These are fall outfits perfect for casual days visiting farms, shopping around charming little towns, and heading out to cozy dinners.

Here’s some new fall pieces I loved wearing this trip…

Flannel Windowpane Plaid Weekender Bag

Shopping around town…

This brown sweater wrap cardigan was great to wear around town popping in and out of shops. I love the Ralph Lauren ranch vibe, and it was so warm. It is a nice alternative to wearing a jacket, and looks great paired with boot cut jeans. I brought my favorite leather and bamboo handbag this trip to carry with all my outfits.

morning hike & visiting farms

The Litchfield Hills has so many great farms, orchards, and roadside markets to visit. We love to just drive and discover new places. I always wear a boot I don’t mind getting muddy or dirty, because many of the farms will have gravel and dirt to walk through. There are some great parks to hike too, so boots are always my go-to when out and about. My bean boots are my go-to for these trips. Also, I keep it casual with a corduroy pant and my favorite Barbour waxed jacket.

Dinner at Arethusa

We had a lovely dinner at Arethusa al tavolo our first night here. The vibe is sweaters with pants and casual dresses. I wore this beige floral maxi dress that has been such a personal favorite this season. I get so many compliments on it, and it is a perfect fall dress to pair with tall boots or a cute suede heel. I brought my tortoise clutch for evenings.

farmer’s market & bookstore morning

We enjoyed a farmer’s market morning followed by a stop at our a favorite bookstore afterwards. It was chilly, and this oversized fisherman sweater and Barbour tartan serape kept me comfortable. I wore my favorite loose ankle jeans paired with a cute velvet flat.

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These are some new favorites that I absolutely loved wearing for this getaway. All of these are great fall staples to wear all season long.

xx Kristy

This post contains affiliate links, which means at no additional cost to you, I may make a commission. I take great care to partner with brands I enjoy, and think you will too. A special thank you to Tuckernuck for collaborating with me on this trip.