Fall Guide to Litchfield County, Connecticut
📍 Litchfield County, Connecticut

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Similar Jacket || Shirt || Pants || Loafers || Similar Handbag || Sunglasses || Earrings
B: Bunny Outfit

Nestled in the rolling hills of Connecticut, Litchfield County is a dream destination for anyone who loves the charm of New England, especially in autumn. Recently, my little family and I took a day trip to soak in the crisp fall air, sip warm apple cider, and explore the area. From classic apple-picking spots to cozy inns, here’s a guide to making the most of Litchfield County this fall.

Stay at the Mayflower Inn

If you’re planning an overnight stay, look no further than the Mayflower Inn in Washington, Connecticut. This luxurious country retreat offers cozy, beautifully decorated rooms from Celerie Kemble make it feel like an extension of the autumn landscape. With a world-renowned spa, fine dining, and over 58 acres of gardens and woodland trails, it’s a place where you can unwind after a day of exploration. Staying here is like stepping into a real-life New England storybook.

Breakfast Arethusa a Mano

For a caffeine fix in Litchfield County, make a stop at Arethusa a Mano in Bantam. This charming coffee shop is an extension of Arethusa Farm and owned by former executives Manolo Blahnik. They serve up delicious coffee, sandwiches, and pastries in a cozy setting. The care and attention to detail that goes into every cup reflects the founders’ dedication to quality, making it a must-visit spot for coffee lovers.

Visit Averill Farm

After breakfast, visit Averill Farm, a quintessential New England farm that’s been family-owned and operated for 10 generations. This historic farm, established in 1746, is famous for its seasonal apple cider, homemade donuts, and fresh pies. The crisp air and beautiful fall foliage made it an ideal spot to enjoy a bit of rustic charm while sipping warm cider. Don’t leave without trying the cider donuts – they’re worth every bite. Visiting this spot will be an annual tradition with Brennan and I look forward to apple picking with her next year.

Shop Small in Litchfield

Litchfield’s shopping scene is a treasure trove of charming boutiques and unique finds. Sister Parish Design is a standout, offering iconic prints, fabrics, and home decor that bring classic American style to life—perfect for adding a stylish touch to any space. For more home inspiration, Milton Market is another favorite, filled with carefully curated antiques and decor items. If you’re looking for something more eclectic, R. Derwin Clothiers is a well-loved spot for upscale men’s and women’s fashion, known for its cozy sweaters and tailored pieces. Another gem is The Hickory Stick Bookshop, an independent bookstore with a fantastic selection of new releases, children’s books, and local authors. Strolling through Litchfield’s quaint streets, you’ll find an array of shops that reflect the area’s artistic spirit and New England charm.

Cider from Hogan’s Cider Mill

Hogan’s Cider Mill, a Connecticut favorite, offers over 20 varieties of hard cider, making it a go-to spot for cider enthusiasts. Since opening its family-friendly Tap Room in 2019, Hogan’s has grown into a beloved destination for both locals and visitors alike. Their signature fall drink, the “Drunken Donut,” is a crowd-pleaser, drawing many to the mill for a unique seasonal treat. Hogan’s expertly combines traditional sweet cider with a creative lineup of cider cocktails, providing a taste of New England charm.

Lunch at White Horse Country Pub

When lunchtime rolled around, we stopped at the White Horse Country Pub in New Milford. Known for its British-inspired pub fare, this spot is beloved for both its food and its decor. Filled with antique furnishings, historic memorabilia, and a cozy fireplace, it feels like stepping into a cozy inn in the English countryside. Be sure to try their fish and chips or hearty shepherd’s pie – both are local favorites and will warm you right up on a chilly day.

Beer at Kent Fall Brewing

For those who love craft beer, a visit to Kent Falls Brewing Company in Kent is a must. Located on a working farm, Kent Falls Brewing produces unique beers with a focus on sustainability and locally sourced ingredients. It’s a great spot to relax and sample a flight of seasonal brews while enjoying the picturesque farm surroundings. With outdoor seating and an easygoing vibe, it’s a great way to wrap up a fall day in Litchfield County.

Our day exploring Litchfield County was magical, filled with incredible food and scenic landscapes, that made it hard to leave. If you’re looking to experience a quintessential New England autumn, Litchfield County offers everything you could want and more. From cider donuts to taking in the fall foliage, it’s the perfect destination for a family day trip.

Love from Connecticut,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England. 

Exploring Portsmouth in LL Bean
📍Portsmouth, NH

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Sweater || Jeans || Loafers || Tote Bag || Earrings

For a crisp fall day exploring the charming streets of Portsmouth, New Hampshire, I kept things cozy and chic with a mix of neutrals and timeless staples. My sweater from LL Bean is the ultimate comfort piece—warm without being too bulky, with a classic knit texture that pairs perfectly with just about anything. I opted for a pair of white jeans, which are my go-to for creating a clean and bright look, even in cooler weather.

One of the highlights of this outfit is my brand-new tassel loafers from J.Crew. These loafers have quickly become a wardrobe favorite, adding a sophisticated touch while being comfortable enough for all-day wear. The tassels give them a playful, preppy vibe, and I love how they complement the relaxed fit of the jeans and sweater.

My husband, David, and I had a quick but wonderful trip to Portsmouth. It was so much fun to see the town through his eyes, as he lived here years ago. We grabbed coffee and breakfast at the cozy Elephantine Bakery, a local spot I highly recommend for anyone visiting. We also stayed at the Hotel Thaxter, which had an amazing blend of historic charm and modern comfort.

This outfit made exploring the historic, coastal town feel effortless yet put together. Whether you’re strolling through colonial Portsmouth or grabbing a quick cup of coffee, it’s a look that strikes the perfect balance between style and practicality. Fall fashion at its best!

Love from New Hampshire,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.