Contrary to popular belief, November might be the best month to travel. Cities across the United States host an array of autumn festivals and events, hotel rates are cheaper, and depending on where you go, you can witness some of the country’s most stunning fall foliage.

All in all, it’s a perfect time to stow away to a cozy town, do a little Christmas shopping, and enjoy a drink next to the fire. Below are three fantastic places to visit around Thanksgiving.

Great Barrington + Lenox, MA 

All of New England is magical in the fall, but nowhere quite so much as Berkshire County. This rural, foresty region of western Massachusetts boasts some of the most stunning fall colors in the world, not to mention an array of charming historic towns.

Some of the best are Great Barrington and Lenox. Spend a few days in these towns around Thanksgiving and you’ll be treated to jaw-dropping foliage, fantastic Christmas shopping and delicious food highlighting New England’s bountiful fall harvest. 

What to Do:

• Shop Main Street

Great Barrington’s downtown is among the oldest in the country, filled with stately Georgian brick storefronts dating as far back as 1853. Today the buildings are filled with an eclectic mix of shops and galleries that reflect the town’s vibrant cultural scene.

Start at Railroad St. Collective, an airy space featuring an array of art and handmade goods from local artists. Closeby is Asia Galleries, which boasts one of the largest and finest collections of antique Japanese goods in the area, at an array of price points.

• Visit Unique Museums

Even if you’re not a museum person, you’ll want to check out some of the world-class, and truly unique museums in the area.

First on the list is The Mount, a 17,000-square-foot neo-Classical mansion and former home of Edith Wharton. It’s special around Thanksgiving, when the grounds are decorated for the holidays.

In the complete opposite direction, we have MASS Moca. This one-of-a-kind museum is housed in a sprawling former printing factory, providing massive exhibition spaces where esteemed artists like James Turrell have shown.

Where to Eat: As with all eateries on the list, make sure to double-check availability on Thanksgiving weekend, when many restaurants close or only serve special menus.

• If you’re visiting the Berkshires, you have to go to Prairie Whale.  This rustic American eatery features locally-sourced ingredients in a constantly changing menu. It’s located in an old Main St. home and oozes ambience, with live jazz most weekends. 

• For more classic Berkshires, it’s worth making the trip to Stockbridge to visit The Red Lion Inn. This landmark tavern has been operating since 1773, and still serves a fantastic (and well-priced) prime rib.

• For something casual, head to Marjoram + Roux, a bright, modern new cafe on Main St. in Great Barrington.

Where to Stay:

• Value: The Constance by the Lenox Collection

This sophisticated B&B features modern touches in a recently-renovated Victorian home. Rates start at $88. Each room boasts stylish decor, plush bedding, and upgraded amenities for a comfortable yet affordable stay. The warm, welcoming staff ensures personalized service, making guests feel right at home. Located within walking distance of downtown Lenox, it offers an unbeatable combination of convenience and charm for budget-conscious visitors.

• Moderate: Cornell Inn

Situated on 4 acres of stunning greenery, this breathtaking hotel is set across three 18th and 19th century buildings. Rates start at $148. Guests can enjoy cozy fireplaces, wraparound porches, and tranquil garden views, creating an inviting atmosphere year-round. A hearty breakfast is served daily, featuring homemade pastries and seasonal specialties. Its proximity to hiking trails, museums, and historic sites makes it a favorite for travelers seeking both relaxation and adventure.

• Pricey: 33 Main 

This beautifully-appointed inn is housed in an 1836 Federal-style home in the heart of Lenox. Prices start at $325 the weekend before Thanksgiving. The interior is a seamless blend of historic charm and contemporary luxury, with custom furnishings and curated art pieces. Guests are treated to a gourmet breakfast featuring locally sourced ingredients, setting a perfect tone for the day. Its central location allows easy access to Lenox’s boutique shops, art galleries, and cultural landmarks like Tanglewood.

Napa Valley, CA

When you think of an ideal autumnal getaway, California might not immediately come to mind. But Napa Valley is the perfect place to visit in November. The lush vineyards turn gold and the valley experiences its best weather year-round, crisp and bright as its famous varietals. 

What to Do:

• Enjoy Holiday Events 

The Calistoga Food & Wine Grand Tasting features a fantastic opportunity to sample some of the best culinary offerings in the region. Over 40 esteemed wineries and restaurants take part in the festival, which takes place on November 16 this year, at the luxurious Solage Resort. 

If you’re in the area after Thanksgiving, definitely take a detour to St. Helena, which hosts an annual tree lighting ceremony in its charming downtown come late November. The 36-foot tree has a distinct local twist– it’s made entirely of wine barrels.

• Go Wine-Tasting 

November kicks off Cabernet season in Napa, when harvest season is over and last year’s reds come to fruition.

Head to Far Niente in Oakville for one of the best cabernets in the region, as well as jaw dropping views of Autumn Gold ginkgo trees that turn red in November.

From November 29 through early December, downtown Napa hosts its annual Winter WINE-derland event. A $100 passport gets you two glasses of wine at over 20 tasting rooms in the area. If you have time, you can visit them all.

Where to Eat:

‍As with all eateries on the list, make sure to double-check availability on Thanksgiving weekend, when many restaurants close or only serve special menus.

• Mustards Grill is one of our favorite low-key eateries in the area. This beloved spot is frequented by local winemakers and chefs, who’ve been enjoying the famous Mongolian pork chop for over 30 years.

• For the best bread of your life, The Model Bakery in St. Helena is not to be missed. Oprah Winfrey reportedly has their world-famous English muffins shipped fresh to her house.

• If you’re in the mood for something more upscale, try PRESS. A fine dining icon in the region, this Michelin-starred restaurant showcases the best in contemporary California cuisine, and holds the largest collection of Napa Valley wines in the world.

Where to Stay:

• Value: Cabernet House

This upscale B&B near downtown Napa is a convenient hub for exploring the region. Rates start at $199. Each room is uniquely designed with thoughtful details, including comfortable furnishings and tasteful decor, to provide a cozy retreat. Guests are welcomed with a complimentary wine hour, perfect for relaxing after a day of tastings. The B&B's proximity to Napa's vibrant downtown ensures access to fine dining, boutique shops, and entertainment without breaking the bank.

• Moderate: Inn on Randolph

Located in a newly restored 1860s Victorian mansion, the Inn on Randolph makes for a picturesque lodging place. Rates start at $300. The property blends historic elegance with modern comforts, featuring heated bathroom floors, plush bedding, and contemporary design elements. Guests can savor a gourmet breakfast made with fresh, locally sourced ingredients in the charming dining room or on the sunlit patio. Its central location in Napa allows easy access to world-class wineries, shops, and restaurants, making it an ideal choice for a romantic getaway.

• Pricey: Farmhouse Inn

This exquisite hotel near St. Helena combines the charm of a country inn with world-class amenities. Rates start at $525. Guests are treated to personalized service, including concierge planning for vineyard tours and private wine tastings. The on-site Michelin-starred restaurant offers a farm-to-table dining experience that highlights seasonal ingredients from local farms. Luxurious suites feature fireplaces, deep soaking tubs, and curated wine selections, ensuring an unforgettable stay in wine country.

Williamsburg, VA

The historic city of Williamsburg draws visitors year-round, but it’s most special around Thanksgiving. Virginia was the site of the first documented Thanksgiving in 1619, when pilgrims sat down to celebrate the fall harvest at Berkeley Hundred Settlement. Just 13 years later and roughly 30 miles away, English settlers established Williamsburg.

Today Williamsburg is still home to buildings and monuments from those years. Especially in the fall, it’s like walking through a history book.

What to Do:

• Visit Colonial Williamsburg

The town’s historic architecture is on full display in Colonial Williamsburg, a stretch of downtown featuring hundreds of original buildings and homes from the 16th to the 19th centuries. The area is officially a museum, with extensive historical activities and exhibitions. 

• Get in Touch with Our Roots

For an even earlier look at the country’s history, head to the Jamestown Settlement. A recreation of America’s first English colony, Jamestown Settlement features an array of fascinating events around Thanksgiving, including the Foods & Feasts of Colonial Virginia festival, which explores the settlers’ culinary traditions.

Where to Eat:

‍As with all eateries on the list, make sure to double-check availability on Thanksgiving weekend, when many restaurants close or only serve special menus.

Williamsburg’s versatile culinary scene includes historic relics and modern new cafes.

• The city’s historic taverns are legendary, and some of them have excellent food. The candlelit Shields Tavern serves a menu similar to when it was founded in the 1740s, drawing influences from the British Empire’s various colonies. 
• Christina Campbell’s Tavern is another good bet, and was reportedly a favorite of George Washington.

• For something decidedly less colonial, head to Pierce’s Pitt Bar-B-Que. A local legend, this family-run spot has been serving some of the area’s best pulled pork and ribs since 1971.

Where to Stay

• Value: Westgate Historic Williamsburg Resort

This traditional hotel features comfortable rooms less than a mile from Colonial Williamsburg. Rates start at $129. The resort offers family-friendly amenities, including a seasonal outdoor pool, fitness center, and game room. Rooms are well-appointed with modern conveniences such as flat-screen TVs, kitchenettes, and free Wi-Fi. Its affordability and proximity to local attractions make it a great choice for families and travelers looking to explore the area on a budget.

• Moderate: Colonial Houses

Just a short walk from the historic center, the cozy Colonial Houses feature a collection of charming Federalist-style guest houses as well as standard rooms in the main residence. Rates start at $203. Each room is thoughtfully decorated with period-inspired furniture, creating an authentic 18th-century ambiance. Guests can enjoy unique experiences like candlelit storytelling and colonial-style breakfasts in nearby taverns. The convenient location provides easy access to the historic district while maintaining a peaceful and quaint atmosphere.

• Pricey: Williamsburg Inn

This luxurious inn has the best location in town, situated in the heart of Colonial Williamsburg. Rates start at $653. Guests enjoy unparalleled elegance with spacious rooms featuring refined furnishings and marble bathrooms. On-site amenities include a world-class spa, fine dining at the Rockefeller Room, and access to championship golf courses. Its proximity to historic attractions allows for an immersive Colonial Williamsburg experience with a touch of modern luxury.

Whether you’re looking to spend Thanksgiving somewhere new, or need a reset vacation after the holiday, November is a perfect time to discover somewhere new. We hope one of these trips will kick off a magical holiday season, or even a new family tradition.