I’m a Connecticut girl, born, raised and stayed. If you love experiencing the four seasons, Connecticut is the place for you. Perhaps our prettiest season is Fall, when our trees turn majestic red, amber, and gold. There is no better place to witness this transformation than in Litchfield County.

Long a pastoral escape for New Yorkers, Litchfield is synonymous with old world New England. Untouched by massive development, Litchfield is an elegant haven for people looking to get away from it all, even if just for the day. 

Where to stay:

Mayflower Inn & Spa, an Auberge Resort, Washington, CT

I love an Auberge Resort. You can be confident that you are getting the best in service and luxury when booking one of their properties.  And it doesn’t  get much better than the Mayflower Inn and Spa.  The cottages in particular are my favorite, with sumptuous beds and every modern amenity you could wish for, while still retaining their charm and elegance. Situated on 58 gorgeous acres, The Mayflower Inn & Spa is the perfect escape.

Photo: The Mayflower Inn and Spa, an Auberge Resort

The Spa at the Mayflower Inn is unparalleled. Aptly named “The Well,” this spa is the ultimate in sophisticated wellness.  Washed throughout in shades of white, it is easy to leave the stresses of everyday life behind.

Photo: The Mayflower Inn and Spa, an Auberge Resort

Winvian Farm, Morris, CT

Have you ever wanted to sleep in a luxurious treehouse? Or maybe in your own 2 story library? Winvian Farms is the perfect marriage of Relais and Chateaux style and imagination. Each of the 18 luxurious cottages has its own theme from the extraordinary to the fantastic. They truly have to be seen to be believed.

As magnificent as the  rooms are at Winvian, and they are magnificent, the true star here is the restaurant. Having earned 5 AAA Diamonds and boasting a 500 label curated wine list, dining here is a one of a kind experience. Even if you can’t get a reservation at the hotel, come for dinner. You will be happy you did. 

Where to dine: 

Arethusa al Tavolo, Bantam, CT 

In my humble opinion, this is quite simply the best restaurant in Connecticut. The food is absolute perfection. The cocktails are sublime. Ambiance is relaxed sophistication and the service is impeccable. Come dressed in jeans or a dress and you will feel comfortable here. Don’t be surprised if you spot a celebrity or fashion icon across the room. A MUST if visiting Litchfield County. Plan ahead as reservations fill up quickly. 

West Street Grill, Litchfield, CT

The grand dame of Litchfield.  A mainstay in the center of town for over 30 years, West Street Grill is a great spot for delicious, sophisticated American fare. Take a stroll around the green, do a little shopping and cap your night off at this modern and cozy gem.

Photo: West Street Grill

Ovens of France, Woodbury, CT

If you’re looking for the most delicious croissants this side of the Atlantic, look no further than Ovens of France.  Baking done as the French do. One bite and you will feel transported to a Parisian cafe. A charming bakery with so much more!

Things to do:

Hiking 

The best way to see the ever changing colors of autumn is to hike one of the many Connecticut trails.  My family and I embraced hiking during the covid lockdown and found it to be one of the best ways to see our state. A friend recommended this wonderful app called “All Trails.” You can narrow your search by location, level of difficulty and read reviews from other hikers who have been to that spot. One of my favorite hiking spots in Litchfield county is the Mount Tom Tower Trail in Washington Depot.

Apple picking

It wouldn’t be autumn in Connecticut without apple picking.  A favorite pastime of young and old alike, some of the very best farms are located right in Litchfield County. Be sure to visit Averill Farm in Washington, CT (which also offers pear picking) and Ellsworth Hills Orchard and Berry Farm (which has a corn maze and a model train display.) I can almost taste those apple cider donuts now…

Shopping

To many, Litchfield county is synonymous with antiquing. Jeffrey Tillou Antiques, right in the center of Litchfield town, is a favorite of many. If you want to go where the designers hang out, then head over to RT Facts in Kent Connecticut.

If you’re strolling through Litchfield center, after admiring its lovely town green, be sure not to miss Oliphant Design for beautiful women’s clothing  and R. Derwin Litchfield for both ladies and gentlemen.

Photo:Christina Febbroriello

Book lovers need look no further than the  Hickory Stick Bookshop in Washington Depot, CT. This is the type of bookstore you could get lost in for hours. Stop by Marty’s Cafe next door for a coffee and some delicious bites and you have yourself a perfect afternoon.

One of my favorite places to shop when visiting the area is Bantam Tileworks. Much more than just tiles, they offer the most exquisite tableware. Stop by before dinner at Arethusa al Tavolo or ice cream at Arethusa Dairy next door.

Finally, I highly recommend “The Market CT” in Bantam. What may seem like your ordinary, run of the mill grocery store, is so much more.  For a small shop, they have an unparalleled selection of fresh produce and prepared food. A perfect place to get whatever you need for a lovely autumn picnic. 

Litchfield County truly has something for everyone, any time of year. But if you’re lucky to visit in Autumn, you will be planning your return trip before you even leave.

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  1. Melissa Rotenberg

    September 27, 2021 at 7:29 pm

    Great inspiration for a day trip over the next few weeks!

    1. Mary Cashman

      September 28, 2021 at 11:04 am

      Thanks Melissa! I’m hoping to go back myself!

  2. Christina Febbroriello

    September 30, 2021 at 4:25 pm

    Great blogpost, Mary! There’s never a shortage of things to do in Litchfield. One thing we just did last weekend was a private tour and bourbon tasting at Litchfield Distillery! I also wish we’d have had enough time for an autumnal horseback ride at Lee Stables! I think I need to move back. Lol

    1. Mary Cashman

      September 30, 2021 at 4:41 pm

      It is really a special place Christina! Love the Bourbon tasting, very the “Yellowstone” series! I’m glad you enjoyed the post!

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