Best Fall Weekend Getaways in the Northeast: Salem, Berkshires, Stowe & Catskills
- Ryan Jones
- Aug 13
- 7 min read
When autumn sweeps across the Northeast, the landscapes transform into a vibrant patchwork of red, orange, and gold. It’s the perfect season to pack a bag and escape for a long weekend — whether you’re drawn to spooky history, mountain views, cozy inns, or farm-to-table dining. Salem, The Berkshires, Stowe, and The Catskills each offer their own unique fall magic, making them ideal destinations for leaf-peeping, seasonal activities, and unforgettable memories. This guide breaks down what makes each spot special, from must-visit attractions to where you’ll want to stay and eat, so you can plan a trip that’s as scenic as it is satisfying.
Salem, Massachusetts – The Halloween Capital of the World
Salem is the quintessential October destination, offering a perfect blend of history, folklore, and festive atmosphere. Known globally for the infamous witch trials of 1692, Salem embraces its heritage with a month-long celebration called Haunted Happenings, which includes parades, markets, live performances, and costume parties. The Salem Witch Museum offers an immersive look at the city’s past, while The Witch House and historic walking tours bring centuries-old stories to life. Visitors can also explore the Salem Maritime National Historic Site or enjoy a leisurely stroll through the cobblestone streets lined with boutique shops and waterfront views.
When it’s time to rest, historic inns and charming boutique hotels offer a cozy stay just steps from the action. Salem’s dining scene is equally inviting, featuring everything from hearty seafood chowders to seasonal pumpkin desserts. Local breweries often roll out autumn-inspired beers, making it easy to toast the season after a day of exploration. While October is undoubtedly the busiest month, visiting in late September or early November can offer a slightly quieter yet equally atmospheric experience.
Hotels to Stay At
The Merchant – Salem, MA | From $350/night
A bold and stylish boutique hotel housed in a historic building dating back to the 18th century. The Merchant blends modern luxury with historic character, offering chic rooms, plush bedding, and a central location perfect for exploring Salem’s attractions on foot.
Hawthorne Hotel – Salem, MA | From $230/night
One of Salem’s most iconic hotels, the Hawthorne has hosted countless guests since 1925. With traditional New England charm, on-site dining, and rumored ghostly encounters, it’s a favorite for travelers seeking a historic stay in the heart of Salem.
The Hotel Salem – Salem, MA | From $200/night
A modern boutique hotel set in a former department store, The Hotel Salem offers vibrant mid-century-inspired interiors and a lively rooftop bar. Its prime downtown location makes it ideal for those wanting a stylish stay within walking distance of Salem’s main attractions.
Salem Waterfront Hotel – Salem, MA | From $220/night
Located along Pickering Wharf Marina, this upscale hotel offers spacious rooms and suites just steps from waterfront dining and shopping. Guests enjoy amenities like an indoor pool and easy access to both downtown Salem and the harbor.
The Berkshires, Massachusetts – Scenic Foliage & Arts
Nestled in western Massachusetts, The Berkshires are a dream for travelers seeking a mix of natural beauty and cultural enrichment. In fall, the region’s rolling hills burst into color, making it a prime spot for scenic drives like the Mohawk Trail or hikes up Monument Mountain. The Berkshires are also rich in artistic and historical attractions, including the Norman Rockwell Museum, MASS MoCA, and The Mount — Edith Wharton’s elegant estate. Quaint towns like Lenox, Stockbridge, and Great Barrington offer boutique shopping, antique hunting, and farm markets brimming with local produce.
Accommodations in the Berkshires range from luxurious spa resorts to charming bed-and-breakfasts, many with fireplaces and mountain views. Food lovers will appreciate the region’s thriving farm-to-table movement, where menus change with the harvest. Crisp apple cider, artisanal cheeses, and hearty autumn fare pair perfectly with the scenery. Fall weekends often bring festivals, craft fairs, and harvest celebrations, making the Berkshires a destination where culture and nature blend seamlessly.
Hotels to Stay At
The Red Lion Inn – Stockbridge, MA | From $250/night
A historic inn that has been welcoming guests for over 200 years, The Red Lion Inn offers cozy rooms, antique furnishings, and a quintessential New England charm. Its location in the heart of Stockbridge makes it a perfect home base for exploring the Berkshires.
The Cornell Inn – Lenox, MA | From $190/night
A charming bed-and-breakfast with uniquely decorated rooms and a warm, welcoming atmosphere. Guests love its hearty breakfasts, beautiful gardens, and proximity to Lenox’s cultural attractions.
Granville House – Great Barrington, MA | From $200/night
A boutique inn blending classic New England architecture with modern comforts. The Granville House offers a peaceful retreat with spacious suites, elegant décor, and personalized service.
The Apple Tree Inn – Lenox, MA | From $210/night
Nestled on a hillside with sweeping mountain views, The Apple Tree Inn is a luxurious yet approachable stay. Guests enjoy refined dining, an outdoor pool, and beautifully appointed rooms just minutes from Tanglewood and hiking trails.
Stowe, Vermont – Foliage Meets Mountain Charm
Stowe is one of New England’s most iconic fall destinations, famed for its postcard-worthy landscapes and cozy mountain-town feel. Situated in Vermont’s Green Mountains, Stowe offers breathtaking foliage views best experienced from the scenic Smugglers’ Notch drive or the Stowe gondola, which carries visitors high above the colorful treetops. Outdoor lovers can hike the surrounding trails, explore covered bridges, or simply wander Stowe Village’s charming shops and cafes. Cold Hollow Cider Mill is a must-visit for fresh cider and warm donuts that perfectly capture the flavors of the season.
Stowe’s accommodations include upscale mountain lodges, family-run inns, and romantic B&Bs, many offering packages designed for leaf-peepers. Dining in Stowe ranges from fine dining establishments to rustic pubs and bakeries serving Vermont maple specialties. Fall also brings local events like harvest festivals, craft fairs, and seasonal brewery releases. For travelers looking to combine relaxation with adventure, Stowe offers the perfect balance in a spectacular autumn setting.
Hotels to Stay At
The von Trapp Family Lodge – Stowe, VT | From $300/night
Owned by the family that inspired The Sound of Music, this Austrian-style mountain resort offers stunning views, cross-country trails, and warm Alpine hospitality. Perfect for those seeking both luxury and charm.
Topnotch Resort – Stowe, VT | From $280/night
An upscale resort with a focus on wellness, Topnotch offers an award-winning spa, indoor and outdoor pools, and easy access to hiking and ski trails. Ideal for travelers who want to unwind in style.
Stoweflake Mountain Resort and Spa – Stowe, VT | From $260/night
A family-owned resort with full-service spa facilities, multiple dining options, and cozy accommodations. Its central location makes it convenient for exploring both Stowe Village and the surrounding mountains.
Field Guide Lodge – Stowe, VT | From $220/night
A chic, design-forward lodge offering a playful mix of modern and rustic elements. Guests love its laid-back vibe, stylish rooms, and proximity to the village’s shops and restaurants.
The Catskills, New York – Rustic Beauty & Outdoor Adventure
The Catskills offer a rustic yet refined escape just a few hours from New York City. In autumn, the region’s mountains, valleys, and forests turn into a kaleidoscope of color, attracting hikers, photographers, and nature lovers. Trails like the one leading to Kaaterskill Falls provide sweeping views and a dose of adventure, while the area’s covered bridges and historic towns add to its timeless charm. Antique shopping in Hudson, exploring art galleries in Woodstock, or taking a scenic rail ride through the mountains are all quintessential Catskills experiences.
Places to stay range from chic boutique hotels to secluded cabins perfect for a quiet weekend retreat. The Catskills are also a haven for foodies, with farm-to-table restaurants, craft breweries, and cider houses dotting the region. Farmers’ markets brim with fresh produce, baked goods, and locally made treats. For those seeking both outdoor adventure and small-town hospitality, the Catskills deliver an authentic and picturesque fall getaway.
Hotels to Stay At
Urban Cowboy Lodge – Big Indian, NY | From $350/night
A design-lover’s dream, this stylish lodge combines modern luxury with rustic mountain elements. Known for its Instagram-worthy interiors, hot tubs, and peaceful forest setting.
Wildflower Farms – Gardiner, NY | From $500/night
A luxury resort surrounded by meadows and mountains, Wildflower Farms offers a high-end wellness experience with spa treatments, farm-to-table dining, and immersive nature activities.
Postcard Cabins – Catskills, NY | From $250/night
Charming cabin rentals offering a cozy, private escape in the heart of nature. Each cabin is uniquely styled, with wood-burning stoves and modern amenities for a romantic or family retreat.
Eastwind Windham – Windham, NY | From $300/night
A Scandinavian-inspired boutique hotel that blends minimal design with warm, rustic touches. Guests can choose from stylish lodge rooms or unique A-frame Lushna cabins, all surrounded by sweeping mountain views. The on-site bar and lounge provide a cozy spot to unwind after hiking or exploring the Catskills.
Final Thoughts – Your Perfect Fall Getaway Awaits
Whether you’re wandering the historic streets of Salem, hiking through the vibrant hills of the Berkshires, soaking in Vermont’s mountain charm in Stowe, or exploring the rustic beauty of the Catskills, each of these destinations offers its own brand of autumn magic. From cozy boutique hotels to seasonal festivals, scenic drives, and unforgettable flavors, the Northeast is at its best when the leaves turn and the air turns crisp.
Fall weekends book up quickly — especially in October — so the sooner you start planning, the better your chances of securing your dream accommodations and activities.
Get Free Help Planning Your Fall Getaway
If you’d like free, personalized help booking and planning your fall weekend escape, I can take care of the research and reservations for you. I’ll help you:
Choose the best destination for your travel style and budget
Find top-rated hotels, tours, and restaurants
Create a custom itinerary so you can enjoy your trip stress-free