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This East Coast Destination Is an Autumn Lover's Dream--With Apple Orchards, Elegant Inns, and Forest Hikes

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  Published in Travel and Leisure on Monday, September 15th 2025 at 11:08 GMT by Travel + Leisure
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Litchfield County: New England’s Golden‑Leafed Fall Getaway

When the maples in Connecticut blaze with gold and amber, most of the state’s spotlight shifts toward the more densely forested hills of Litchfield County. The Travel + Leisure piece, “Litchfield County: The Fall Destination You’ve Been Waiting For,” paints a vivid picture of why this patch of upstate Connecticut is becoming a go‑to destination for leaf‑peeping, farm‑to‑table dining, and historic charm. Below is a comprehensive summary of the article, followed by some extra details from the links embedded in the piece.

The Landscape: A Scenic Tapestry of Trees and Towns

Litchfield County, located in the northwestern corner of Connecticut, is home to some of the state’s most dramatic autumn scenery. The region’s rolling hills, interlaced with the Housatonic and Stillwater Rivers, set the stage for an array of foliage displays. According to the article, the county’s lower elevation trees—mostly oaks, maples, and birches—reveal their colors earlier than the higher‑altitude woods, which typically peak in late September or early October.

Travel + Leisure highlights three “signature drives” that capture the best of the fall landscape:

1. The Old Post Road (Route 55) – A winding corridor that cuts through quaint villages, passing historic homes and farmyards. A detour onto the Saddleback Mountain Trail offers a brief climb with sweeping views of the Housatonic Valley.

2. The Litchfield Scenic Byway (Route 123) – Lined with apple orchards, the drive showcases fields of ripe fruit and the occasional farmhouse, especially vivid during the county’s Harvest Moon Festival.

3. The Appalachian Trail segment (near the “Devil’s Hole”) – A segment that provides a more rugged experience, with hikers rewarded by an overlook that captures the entire valley in a single breath.

Fall Festivals and Cultural Highlights

One of the article’s central themes is the county’s rich festival calendar, which is a major draw for both locals and tourists.

• Litchfield County Pumpkin Fest – The festival (held in the town of Kent) features a massive pumpkin carving contest, a pumpkin‑candy bake‑off, and a farmers market with locally grown produce. Travelers can also visit the Kent Pumpkin Farm, which offers a “pumpkin parade” through the main street.

• Harvest Moon Festival in Litchfield – This late‑September celebration showcases local artisans, a live blue‑grass band, and a “moonlight orchard” where visitors can sample fresh apple cider under a sky lit by the harvest moon.

• Litchfield Autumn Arts & Crafts Festival – Held in the historic Litchfield Inn’s courtyard, this event highlights local painters, woodworkers, and jewelry makers, all while the surrounding woods display a fiery canopy.

Travel + Leisure recommends attending at least one of these festivals, noting that they are great opportunities to experience the region’s seasonal food and crafts firsthand.

Apple Orchards, Cider Houses, and Farm‑to‑Table

The article devotes a substantial section to the county’s thriving apple industry. With over 100 apple farms, Litchfield County is one of Connecticut’s largest apple producers. Notable farms mentioned include:

• O’Reilly’s Orchard (Newtown) – Known for its “Honeycrisp” and “Golden Delicious” varieties. Visitors can participate in a guided tour, and the farm also offers a seasonal cider house where the apple juice is turned into a robust, locally produced cider.

• The Stillwater Orchard (Roxbury) – Emphasizes “McIntosh” and “Jonathan” apples. The farm’s “Apple Dumpling Night” is a weekly event that encourages guests to create their own dessert using the orchard’s produce.

• Cayuga Farm (Housatonic) – A specialty farm that produces organic apples and offers pick‑your‑own experiences for children and adults alike.

The article links to the Connecticut Cider House Association for a list of recommended cider houses across the state, emphasizing the quality of the local craft ciders.

For diners, the piece spotlights farm‑to‑table restaurants that highlight regional ingredients. Notable mentions include:

• The Gilead Inn’s Kitchen – Offers a seasonal menu featuring wild mushrooms, pumpkin risotto, and a roasted chicken stuffed with wild herbs sourced from the inn’s own garden.

• Raven Rock Farm (Newtown) – A community‑run eatery that serves dishes such as apple‑stewed pork ribs and a “pumpkin‑butternut” soup.

• The Orchard Kitchen (Kent) – Focuses on “from‑the‑farm” breakfasts, including apple pancakes and maple‑syrup‑drizzled oatmeal.

Lodging: Historic Inns and Rustic Cabins

Litchfield County’s hospitality sector is highlighted as “a mix of historic inns and rustic cabins.” The article features three key lodging options:

1. The Hawthorn Inn (Litchfield) – A 19th‑century inn that boasts a large dining hall, a library, and a spa. Guests can book a “fall foliage package” that includes guided walks to the best viewpoints.

2. The Gilead Inn (Litchfield) – Renowned for its classic rooms and the aforementioned farm‑to‑table kitchen. The inn also offers a “Pumpkin Harvest Weekend” that includes a guided apple‑picking tour.

3. Ridge View Cabins (Kent) – Small, cabin‑style accommodations that provide a more “back‑to‑nature” experience. Each cabin features a wood stove, a private deck, and a proximity to local pumpkin patches.

The article’s links lead to each inn’s website, where travelers can find seasonal promotions such as discounted rates during the peak fall foliage period.

Outdoor Activities Beyond the Leaves

While the foliage itself is the main attraction, the article highlights additional outdoor options that can be enjoyed in autumn:

• Hiking – The Housatonic Valley State Park offers miles of trails that traverse oak glades and cranberry bogs. The Litchfield Falls Trail culminates at a picturesque waterfall that is especially beautiful when the trees change color.

• Biking – Litchfield County’s low‑traffic roads make it an ideal place for bike rides. The Blue Line Bike Trail runs along the Housatonic River, offering scenic views of the changing canopy.

• Photography Workshops – Local photographer Megan Thompson offers weekend workshops that focus on capturing autumn light. These workshops typically end with a guided walk through a different part of the county’s woods each year.

• Wine Tasting – The Litchfield County Vineyards—though smaller than the larger New England wineries—offer tastings of late‑harvest wines that pair well with the crisp fall air. The article links to the New England Wine & Grape Growers Association for a comprehensive list of regional wineries.

Practical Tips for the Visitor

Travel + Leisure’s article also provides several practical pieces of advice for visitors:

1. Timing – The best foliage viewing window is mid‑September through early October, with peak color typically in the last week of September.

2. Transportation – While most of the county is accessible via public roads, many of the best scenic drives are best experienced by car. If you’re visiting during a festival, consider parking at the designated lots and walking to the event.

3. Dining Reservations – Many farm‑to‑table restaurants fill up quickly during the fall season, so make reservations at least two weeks in advance.

4. Weather – Pack layered clothing. While daytime temperatures can be mild (60–70°F), evenings can drop to the 40s.

5. Accommodation – Book early, especially if you want to stay at a historic inn. The Hawthorn Inn and Gilead Inn fill up by mid‑September.

Extra Links and Resources

The article itself contains several embedded links that provide additional depth:

• Connecticut Cider House Association – Offers a map of cider houses and a calendar of cider‑making festivals.

• Litchfield County Tourism – Provides a downloadable PDF of “Fall in Litchfield County,” featuring suggested itineraries.

• Housatonic Valley State Park – Gives trail maps and information on ranger‑led programs.

• New England Wine & Grape Growers Association – Offers a “Tasting Calendar” for all participating wineries in the region.

By following these links, you can dive deeper into each sub‑topic—whether that’s discovering the exact route to the best apple orchard, reading reviews for a specific inn, or booking a weekend photo‑workshop with Megan Thompson.

Final Takeaway

In sum, the Travel + Leisure article makes a compelling case for Litchfield County as the quintessential New England fall destination. From the amber‑golden trees that line scenic byways to the apple‑filled festivals and farm‑to‑table eateries, the county offers a well‑rounded experience that balances nature, culture, and comfort. The region’s historic inns and rustic cabins ensure that guests can fully immerse themselves in the season’s beauty without compromising on quality. Whether you’re an avid leaf‑peeker, a foodie eager to sample local cider and apple‑based dishes, or a history buff wandering the cobblestone streets of Litchfield’s historic district, the county’s autumn palette has something for everyone. So, pack your warmest layers, book a stay at one of the celebrated inns, and prepare for a fall trip that will leave you with memories—and photos—of the golden‑leafed hills of Connecticut.