Scenic Connecticut Towns to Visit for a Taste of the Fall Harvest

Described as one of Connecticut’s most picturesque fall towns, Litchfield has everything from covered bridges and sugar maple trees to apple picking and stunning fall foliage. When it comes to things to do in Connecticut in the fall, Averill Farm tops our list for apple picking. If you’re looking to have some happy hour fun, Hogan’s Cider Mill serves up delicious hard cider as well as other harvest goods. In Warren, you’ll find another of our favorites: Angevine Farm, the perfect place to scope out the fall produce and grab some pumpkins for carving. 

Stay in the area at Lost Fox Inn. Nestled just outside of Litchfield, this gem is a historic 1740s tavern that has been meticulously transformed into a refined boutique hotel, seamlessly blending its rich colonial heritage with modern luxury. Their on-site tavern and restaurant offers a sophisticated dining experience, featuring locally sourced ingredients and seasonal menus. 

Another favorite? The Litchfield Inn is a crowning reproduction of a classic colonial estate that pays tribute to the historical distinction of the town without sacrificing the modern amenities of today. Family owned and operated, they have welcomed guests from all over the world with warmth and hospitality for over 40 years.

Farmington makes a great autumn base in the heart of the Farmington Valley, starting with crisp foliage strolls and exploring across the historic grounds of the Hill-Stead Museum. Just minutes away, gather seasonal produce at Avon's Pickin’ Patch, or drop by Rosedale Farms in Simsbury for local Connecticut Wine Trail harvest events. For the ultimate seasonal perspective, take a quick hike up Talcott Mountain to Heublein Tower for panoramic views of the red, oranges, and yellows below.

In search of a great place to stay in the area? We adore The Goodwin in nearby Hartford. Once a landmark 19th-century residential building, this boutique hotel uniquely fuses the history of Connecticut’s capital city with contemporary style. It truly is a cultural experience that combines elegance, modern comforts, and personalized hospitality. In West Hartford, you’ll find DELAMAR, the capital region’s premier boutique luxury hotel. Located at the center of Blue Back Square and complete with bike rentals, a relaxing spa, and elevated fitness center, this is the perfect spot for a fall getaway.

One of our favorite Connecticut fall vacation locations is Mystic, home to B.F. Clyde's Cider Mill. Known for cider donuts and apple slushies, this family-owned and operated establishment is the oldest steam-powered cider mill in the United States. Every September 1st, they open their doors and sell sweet cider, hard cider, wine, cider donuts, and many local goods. Expect cider-making demonstrations, wine and hard cider tastings, and a new obsession with their renowned cider donuts. If you’re looking to do some pumpkin picking, Whittle's Willow Spring Farm is our go-to and after a visit, you’ll see why. 

While in Mystic, stay at the waterfront Steamboat Inn for relaxing coastal New England views or Captains Mansion, a beautifully preserved historic inn in the heart of Mystic. Both showcase an elegant marriage of rich maritime history and welcoming hospitality making it impossible to go wrong this fall.  

We would be remiss if we didn’t highlight Guilford, a town that features shoreline charm and is anchored by the historic Guilford Town Green (a quintessential Connecticut must-visit in autumn). Browse handmade works at the Guilford Art Center, then head over to Bishop’s Orchards for a classic harvest day, complete with pick-your-own fall produce, a bustling farm market, and fresh local cider. Talk about the perfect fall outing.

Stay in the nearby charming coastal town of Madison after venturing around Guilford for the day. The Homestead Bed & Breakfast offers a welcoming retreat for relaxation and exploration that’s close to the beaches, boutique shopping, and sumptuous restaurants. Or, opt for Madison Beach Hotel, nestled directly on the Long Island Sound, as this property adds a touch of coastal luxury to your fall escape. 

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