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THE PERFECT 3-DAY ITINERARY TO EXPLORE WESTERN MASSACHUSETTS

For a storybook getaway in the midst of the holiday season, it is hard to go past Western Massachusetts. With its historic charm, holiday light displays, and, thanks to Dr. Seuss, ties to the Grinch, Western Mass. has everything you could need to immerse yourself in the holiday spirit. 


Wondering how to get there? The Peter Pan Bus Company is a great option. Just 35 minutes from Hartford, CT., and with options direct from Boston and New York, take the chance to really see the scenery along the way and travel by coach. 



Once you arrive, here’s my recommendation for a 3-day short getaway to Western Massachusetts that is sure to put the wonder in the most wonderful time of the year.


Day One: Springfield


Springfield, famous for being the birthplace of Theodore Geisel (more commonly known as Dr. Seuss), is also home to the first resort casino in the Commonwealth of Massachusetts. The MGM Springfield complex knows how to get in the festive mood, with the city’s only outdoor skating rink and tasteful decorations throughout. Whether you get your skates on or just enjoy the atmosphere with a hot chocolate to keep you warm, the rink should definitely make your list of places to spend time on day one.


Inside the resort complex, there are a multitude of dining options. While there are several more formal restaurants on site, try the South End Market dining hall for a casual eating experience. I can personally recommend the lobster rolls and General Tsao’s chicken at Flights!


MGM Springfield offers modern amenities and classic style, and the rooms are all spacious yet feel cozy, with luxurious fittings and sleek design. With everything you need to have a comfortable night in and a location that has a night out practically on your doorstep, the MGM Springfield is an excellent hotel choice to start your getaway with.


While you are waiting to check in to your hotel room, head along to the Springfield Museums and check out the Grinch’s Grotto. Head to the cave in the midst of Who-ville and get a picture with the green guy himself! Once you’ve got your pic, take some time to check out the entire complex - the Dr. Seuss National Memorial Sculpture Garden, the Amazing World of Dr. Seuss Museum, and the Lyman and Merrie Wood Museum of Springfield History are just a few of the highlights. Be sure to check out the Black Panther statue while you’re there, too - the tribute to Ruth E. Carter, Springfield native and the first African American woman to win the Oscar for best costume design when she took the Academy Award in 2019 for her work on the Marvel movie, is really something! 


When visiting Springfield in December, you cannot afford to miss the Bright Nights in Forest Park. This incredible light display has been coming to Springfield every Christmas since 1995, with over 7 million visitors so far. More than just a light display, there are horse-drawn carriage rides, choral concerts, and a visit with Santa available at this winter wonderland.


Before heading back to the MGM Springfield Hotel for the night, stop in and experience the Bavarian atmosphere at the Student Prince and the Fort. With carolers on site every day from December 1st to Christmas Eve, this German-style tavern is sure to get you in the Christmas mood with its hearty fare and festive decor. Once you’ve filled your cup and your belly, make your way back to the hotel for an early night or take a detour into the casino and have a play on the tables. 



Day Two: Historic Deerfield & Stockbridge


On your way out of Springfield, be sure to stop in at Granny’s Baking Table. This small-batch bakery is some kind of special, with hot drinks and warm smiles, delicious pastries, and a welcoming atmosphere that really does feel like you’re at Granny’s table. Have a seat, or grab some deliciousness to go - either way, this will be a memorable stop!


As you head north towards Deerfield, the first stop has to be the Yankee Candle Village in South Deerfield. Visit with Santa, spend time immersed in the divine scents of the season, and wander through the Bavarian village, complete with indoor snow and 25 25-foot Christmas tree. This is the perfect stop to top up that festive spirit and purchase a gift or two for loved ones - or yourself!


Before you take in more of the local sights, grab a quick bite at Champney’s Restaurant and Tavern at the Deerfield Inn. The Inn is a quaint historic building with loads of charm, and Champney’s knows how to do great food and exceptional hospitality. The lobster roll is a personal favorite, but the menu is diverse and delicious across the board, so you’re sure to find something you love here.


While you let your lunch settle, take a ride on a horse-drawn carriage through Historic Deerfield. This outdoor museum features twelve carefully preserved houses dating from 1730 to 1850, complete with handmade wreaths hung on the front doors for the holidays. There are guided tours available, and the guides are all so friendly and informative that you won’t want to leave this gorgeous historic town. 


When you are finally able to tear yourself away from the history of Deerfield, a short hour away is the town of Stockbridge, MA. Stockbridge is home to the Red Lion Inn, a gorgeous traditional inn with a rich history. The Red Lion is quintessential New England, a picture-perfect town made famous as a favorite subject for Norman Rockwell’s work. 


Before grabbing some dinner at the friendly local dining spot, Alta Restaurant and Wine Bar, bundle up and take in the sights of the Winterlights at Naumkeag. This incredible stately home is nestled in a 48-acre estate, and every year it offers a magical outdoor experience featuring thousands of lights. 


Alta Restaurant and Wine Bar is the perfect place to finish off a busy day of sightseeing. The food is exquisite, the atmosphere is cozy and cute, and the service is exceptional. Just 5 miles from Stockbridge, in the small town of Lenox, MA., Alta is a slice of the Mediterranean in New England. 


Day Three: Stockbridge And Lenox


Before you leave the town of Stockbridge, be sure to pop into the Norman Rockwell Museum. Rockwell put Stockbridge on the map of American Art history, and his work is celebrated in style across a 36-acre campus with 10 galleries. Worth a visit to see his Saturday Evening Post covers - all 323 of them!


Head back to Lenox and the incredible Ventfort Hall. Listed on the National Register of Historic Places, Ventfort Hall is home to the Museum of the Gilded Age and is an exceptional example of Jacobean architecture that cannot be missed, especially when it is all dressed up for the holiday season! The staff and volunteers do an amazing job of decorating the mansion, and it truly is a magical way to finish off the sights of Western Massachusetts on your holiday getaway.


Before you head home, stop in at the Haven Cafe and Bakery on Franklin St, Lenox. Open for breakfast, brunch, and lunch, this cafe is the home of Shelly Williams and her team of dedicated bakers who work from the early morning hours to bake the most delicious bread and baked goods. The perfect place to dine before your trip home.


Western Massachusetts is a truly beautiful region with historic charm, festive spirit, and exceptional hospitality. If you’re looking for a short holiday getaway to escape the craziness of the season, you cannot go past the lovely towns of Western MA. area. Happy Holidays!