Western Massachusetts comes alive with festive charm during the winter holidays. From historic inns and cultural attractions to enchanting holiday activities, this guide will help you make the most of your winter getaway in this picturesque region. My family has been visiting this fabulous area for years. We’ve made cherished memories skiing at Jiminy Peak and Butternut, visited The Amazing World of Dr. Seuss Museum and, my youngest son actually attended Springfield College in his freshman and sophomore years. It’s a wonderful destination all year round but it’s especially so during the holidays and winter months. Read on to see the best places to stay, eat, and play to experience a Winter Wonderland in Western Massachusetts.
Where To Stay:
The MGM Springfield hotel is a premier entertainment destination in the heart of Springfield, Massachusetts. With its stylish accommodations, a full-service casino, diverse dining options, and exciting nightlife, it offers a complete experience for visitors seeking both relaxation and entertainment. Located in a historic and culturally rich area, the hotel is not only a place to stay but also a hub for memorable experiences, making it a must-visit destination for those exploring Western Massachusetts.
Nestled in the heart of Stockbridge, the Red Lion Inn is a quintessential New England retreat. Here’s what you can expect during your stay:
- Historic Ambiance: The Inn’s colonial-style architecture and antique furnishings create a warm and welcoming atmosphere.
- Dining Delights: Savor locally-sourced cuisine at the inn’s renowned restaurants, featuring classic New England dishes. With four different dining locations to choose from; The Main Inn, Widow Bingham’s Tavern, The Courtyard (weather permitting), and The Lion’s Den you’re guaranteed to have a deliciously memorable meals!
- Festive Decorations: Experience the Inn’s charming holiday decor, complete with wreaths, lights, and a beautifully decorated Christmas tree in the lobby.
Where To Eat:
Champney’s Restaurant & Tavern at the Deerfield Inn
As a diner at Champney’s Restaurant & Tavern, you’re in for a treat that captures the essence of New England cuisine and hospitality. From the moment you walk through the doors, you’ll be enveloped in an atmosphere that exudes comfort and authenticity. Sink into plush chairs, bask in the glow of crackling fireplaces, or perch yourself at their exquisite eighteen-seat mahogany bar. Their commitment to local sourcing shines through with an array of twelve local draft beers, an extensive selection of wines by the glass, and a menu that changes with the seasons, showcasing the best of local farms.
Alta Restaurant & Wine Bar
Alta Restaurant & Wine Bar became a part of the picturesque Lenox village in the summer of 2008. Established by three passionate restaurateurs, Alta has since become a beloved dining destination, cherished by both locals and visitors alike.
With a dinner menu that celebrates local and organic ingredients, the Mediterranean-inspired cuisine is a testament to freshness and flavor. Complementing the culinary offerings is an extensive wine list featuring selections from around the world, boasting an impressive array of 24 wines available by the glass. This blend of inspired Mediterranean dishes and wines from diverse regions creates a welcoming and familiar dining experience.
At Alta, the commitment extends beyond the plate and the glass. Alta takes pride in providing exceptional service, ensuring that every visit is a memorable one.
Haven Cafe & Bakery
At Haven Cafe & Bakery, dedication to top-quality food and excellent service for all guests is paramount. Whether you need of a fresh cup of coffee on the go, a healthy and delicious sit-down breakfast, a flavorful meal to take home, or help with planning a catered event for a large group, patrons can expect top notch service with a smile! Haven proudly supports a network of local organic farmers and environmentally conscious distributors. This commitment ensures that every dish and beverage served there is not only a delight for the palate but also reflects a strong dedication to quality and sustainability.
Granny’s Baking Table
Nestled in the heart of Springfield, Granny’s Baking Table is a culinary haven that pays homage to a bygone era, where baking was an art form and the dining table served as a gathering place for meaningful conversations.
Granny’s proudly melds two distinct baking traditions—the warmth of the American South and the craftsmanship of Northern Europe. With an unwavering dedication to the authentic craft of small-batch baking, Granny’s Baking Table brings you a delightful fusion of flavors and techniques that transport you to simpler times.
The vision behind Granny’s Baking Table is brought to life by the partnership of artisan bakers Sonya Yelder and Todd Crosset. They share a profound commitment to their craft and to the vibrant community of Springfield. In every delectable creation, you’ll find a celebration of the diversity and richness that defines the community.
At Granny’s, they understand the universal desire for human connection. The establishment is more than a bakery; it’s a place where people come together over lovingly crafted baked goods to savor not only the flavors but also the moments of connection that make life truly meaningful.
Student Prince and The Fort
Dating back to 1660, this historic site in Springfield once housed a fort constructed by John Pynchon to protect the settlement. Fast forward to 1935, and the Student Prince emerged as a Springfield icon. Originally just a bar with a modest collection of beer steins, it expanded to include a dining room in 1946. Rupprecht Scherff, who joined the restaurant in 1949 and took ownership in 1961, became the heart and soul of this local institution until his passing in 1996. Under the Scherff family’s stewardship until 2014, the Student Prince flourished, becoming synonymous with special occasions and family traditions. In 2014, Rudi Scherff announced the restaurant’s closure, but a group of dedicated local business owners, led by Peter Picknelly, stepped in to preserve its legacy. While making necessary upgrades, they honored the establishment’s rich history. Today, the Student Prince continues to serve as a cherished gathering place, embodying a tradition of excellence that spans generations.
Where to Play:
Norman Rockwell Museum
A warm and inviting experience awaits you at the home of American illustration, inspired by the timeless legacy of Norman Rockwell. Step into a world of artistic wonder as you marvel at Rockwell’s full-size original paintings, gaze upon all 323 of his iconic The Saturday Evening Post covers, and become enchanted by special exhibitions that showcase the incredible artistry of both past and present illustrators. With 10 captivating galleries, engaging programs, and a beautiful 36-acre campus to explore, there’s always something new to discover. Make the most of your visit by reserving your tickets online in advance, ensuring you access to the lowest prices and securing your spot for visits through April 30, 2024. Don’t miss this opportunity to immerse yourself in the rich tapestry of American illustration history.
Step into a world of grandeur and history at Ventfort Hall, an awe-inspiring Jacobean Revival-style mansion constructed in 1893 for none other than Sarah Morgan, sister to the renowned J. P. Morgan. This magnificent mansion, listed on the National Register of Historic Places and endorsed as an official project of “Save America’s Treasures,” a Millennium initiative by Hillary Rodham Clinton and the National Trust for Historic Preservation, now proudly houses The Museum of the Gilded Age.
Ventfort Hall stands as one of the remarkable “Cottages” that graced Lenox during the late 19th century, when the village emerged as a favored Gilded Age resort destination. The Museum of the Gilded Age offers a captivating glimpse into the transformative changes that unfolded in American life, industry, and society during the 19th century—a truly fascinating period in American history. Come and explore the opulence, elegance, and cultural significance of Ventfort Hall, and embark on a journey through a bygone era that continues to captivate visitors to this day.
Winterlights at Naumkeag
During this festive holiday season, the enchanting gardens surrounding the beloved historic residence, Naumkeag, in Stockbridge, will come alive with a brilliant display of thousands of glistening holiday lights. For three consecutive years, Winterlights at Naumkeag has earned the prestigious recognition from USA Today as one of the most outstanding public holiday lights exhibitions in the nation. The Winterlights will be on display until January 6th ( Wednesday – Sunday 4:30pm until 8:30pm)
Nestled in the heart of New England, Historic Deerfield, established in 1952, invites visitors to step back in time and immerse themselves in the rich history and culture of early New England and the Connecticut River Valley. Explore a curated collection of twelve meticulously preserved antique houses dating from 1730 to 1850, each offering a glimpse into a bygone era. Marvel at world-class exhibits featuring regional furniture, silver, textiles, and decorative arts within these authentic period houses and the state-of-the-art Flynt Center of Early New England Life.
During the holiday season, experience a Christmas unlike any other, inspired by the 18th and 19th centuries when December was a time of weddings, social gatherings, and festive celebrations. Witness the charm of Old Main Street adorned with natural, hand-crafted wreaths, paying homage to the era when Christmas trees were a novelty.
For guests seeking a romantic getaway, the Deerfield Inn in the Historic Village of Deerfield, MA offers an enchanting experience. From now until the end of the Fall season, enjoy magical carriage rides on Friday, Saturday, and Sunday evenings. Let JB, a magnificent white Percheron, whisk you away down the quaintest street in New England. Snuggle in an elegant, fringed surrey with your companion as you clip-clop past Deerfield’s Historic District and picturesque meadows, creating cherished memories in this idyllic setting.
Yankee Candle Village
Take a leisurely walk through the enchanting Bavarian Village, where you’ll discover an array of delightful treasures. Explore an extensive collection of ornaments, including exclusive Grinch merchandise, immerse yourself in festive scents that capture the essence of the season, and even have the chance to meet Santa himself. At Yankee Candle Village, the spirit of the holidays is lovingly preserved throughout the year, creating a magical destination that promises something special for everyone.
Nestled in South Deerfield, Massachusetts, the Yankee Candle flagship store beckons with its charm and allure, drawing an impressive three million visitors annually. It proudly stands as one of the state’s premier tourist attractions.
Bright Nights at Forest Park
Get ready for a spectacular 29th season of Bright Nights at Forest Park, and you won’t want to miss the grand celebration for its big 30th anniversary next year! This annual event features a mesmerizing lighting display that transforms a scenic three-mile drive into a winter wonderland. Be sure to explore the enchanting section dedicated to the beloved Dr. Seuss and the mischievous Grinch.
But that’s not all! Dive into the magic of Santa’s Magical Forest, where you can savor delicious food and beverages while taking a delightful whirl on the carousel. Bright Nights promises a magical experience for all ages, making it the perfect holiday tradition. The lights are on display until January 1st.
Amazing World of Dr. Seuss Museum
Step into the whimsical world of the Grinch at the exclusive Grinch’s Grotto, a truly immersive experience available only at the Springfield Museums. Here, you’ll have the rare chance to meet the Grinch himself in his special cave, where you can snap some memorable photos and enjoy interactive stations that promise fun for the entire family. The Grinch’s Grotto is set in a lively Who-ville space, adding to the charm of the encounter.
After your Grinch adventure, take some time to explore the captivating Dr. Seuss National Memorial before venturing into the rest of the complex at your own pace. Grinch’s Grotto runs through January 14th but there’s so much to see and do all year round. The Springfield Museums, conveniently located in downtown Springfield, Massachusetts, offer year-round access to five world-class museums, including the Amazing World of Dr. Seuss Museum and the Dr. Seuss National Memorial Sculpture Garden.
As we wrap up our journey through Western Massachusetts, it’s clear that this region is a treasure trove of holiday delights and year-round attractions. Whether you’re seeking a cozy retreat at The Red Lion Inn or the MGM Springfield’s vibrant entertainment, savoring the culinary excellence at Champney’s Restaurant & Tavern or Granny’s Baking Table, or immersing yourself in the world of American illustration at the Norman Rockwell Museum or the timeless charm of Ventfort Hall, there’s something to captivate every traveler’s heart. Don’t miss the festive brilliance of Winterlights at Naumkeag, the enchanting historic experience at Historic Deerfield, and the magical world of Dr. Seuss at the Springfield Museums. Bright Nights at Forest Park and the exclusive Grinch’s Grotto add to the holiday magic, while Jiminy Peak Resort and Ski Butternut offer winter sports enthusiasts an exhilarating adventure. Western Massachusetts welcomes you year-round, promising unforgettable memories in every season.