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Massachusetts By Rail

Massachusetts By Rail

Massachusetts By Rail

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  • Guests: 2 Adults
  • Duration: 9 Nights
  • Board: Room Only | Bed & Breakfast
  • Departing: Selected UK Airports
  • Offer Date: 19th September 2025

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Look forward to an amazing nine-night adventure on this Massachusetts by Rail holiday! This round-trip by rail begins and ends in Massachusetts’s capital city of Boston. Your journey lets you experience the state’s eclectic mix of history, cuisine, activities, and scenery; alongside the opportunity to visit famous sights and attractions of not only Boston but also Worcester, Springfield, Pittsfield, Greenfield, and Northampton.

Day One: Boston, Massachusetts

Fly into Boston where your nine-night adventure gets underway with an overnight stay at Aloft Boston Seaport Boston. You’ll have plenty of time to explore Massachusetts’ capital. Perhaps take a leisurely walk from Boston Common along the 2.5-mile-long Freedom Trail and discover the 16 historic sites and monuments lining the route. Get up close to marine life at New England Aquarium or see the exhibits at Museum of Fine Arts Boston, Museum of Science, and John F Kennedy Presidential Library and Museum. Indulge in retail therapy at Faneuil Hall Marketplace and Quincy Market. Cheer on Major League Baseball’s Boston Red Sox at Fenway Park.

Day Two: Worcester, Massachusetts

Check out of your hotel in time to catch the 12:50 train from Boston South Station to Worcester, arriving at 14:00. Check into Homewood Suites by Hilton Worcester for an overnight stay. Maybe pay a visit to the indoor/outdoor EcoTarium complex with its digital planetarium, wildlife exhibits, tree-top walkway, and narrow-gauge railway. Go to see Worcester Art Museum’s vast collection of Roman mosaics, medieval armour, and Impressionist paintings. Stop by the museum in the restored 18th-century, Georgian-style Salisbury Mansion or leave the city behind to step back in time to the early 1800s at Old Sturbridge Village living history museum.

Days Three to Four: Springfield, Massachusetts

Today’s rail journey at 14:06 takes you to Springfield, Massachusetts; arriving at 15:21. Hilton Garden Inn Springfield is your home for the next two nights. Springfield sits on the east bank of the Connecticut River and is your gateway to meeting the exotic animals at the Zoo in Forest Park and exploring all things basketball at the Naismith Memorial Basketball Hall of Fame. Spend time at Springfield Museum with its Amazing World of Dr. Seuss Museum, Dr. Seuss National Memorial Sculpture Garden, George Walter Vincent Smith Art Museum, Springfield Science Museum, Michele and Donald D’Amour Museum of Fine Arts, and Lyman and Merrie Wood Museum of Springfield History.

Days Five to Six: Pittsfield, Massachusetts

Board the train in Springfield at 15:26 bound for Pittsfield, the Berkshires’ largest city; arriving at 16:42. Check into Hilton Garden Inn Lenox Pittsfield for the following two nights. You’ll have chance to explore Berkshire Museum’s art, science, and history and meet wildlife in the Aquarium, step back to bygone times at Hancock Shaker Museum, and visit author Herman Melville’s Arrowhead home where he wrote ‘Moby Dick’. Witness the artistic process and be captivated by the artworks on display at Clock Tower Artists and Lichtenstein Center for the Arts. Or why not visit Edith Wharton’s Home, the Mount, or Ventfort Hall Gilded Age Museum in nearby Lenox?

Day Seven: Greenfield, Massachusetts

Board the train in Pittsfield at 16:30 and travel indirect via Springfield to Greenfield; arriving at 22:33. Check into Hampton Inn & Suites Greenfield for an overnight stay. Perhaps take a leisurely climb up to Poet’s Seat Tower for amazing views and then walk along the nearby Pocumtuck Ridge Trail. Wander along Main Street in Downtown Greenfield, escape to the Magic Wings Butterfly Conservatory and Gardens, or stroll over the Bridge of Flowers and under the Historic Eunice Williams Covered Bridge. Explore the region’s rich industrial history at Museum of Our Industrial Heritage and learn out about the Connecticut River Watershed at the Great Falls Discovery Center.

Day Eight: Northampton, Massachusetts

Today, your 13:36 rail journey takes you to Northampton, arriving at 14:01. Here you’ll check into Quality Inn & Suites Northampton - Amherst for an overnight stay. Wander through the idyllic Smith College Botanic Garden and admire the 27,000+ artworks on display at Smith College Museum of Art. Pay a visit to the Calvin Coolidge Presidential Library Collection at Forbes Library and explore local history at the Historic Northampton Museum. Ride the 15-inch gauge miniature railway or get up close to deer, peacocks, pygmy goats at Christenson Natural Wildlife Center in Look Park. Amble along Main Street or treat yourself to scented candles at the Yankee Candle Village in nearby South Deerfield.

Day Nine: Boston, Massachusetts

Early afternoon, you’ll catch the 14:01 indirect train from Northampton via Springfield back to Boston, arriving at 20:24. Check into Staypineapple, A Delightful Hotel in South End Boston. Perhaps you’ll have time to retrace portions of the Freedom Trail; taking in Boston Common, King's Chapel, the Boston Massacre site, and the many pubs and taverns where America's Founding Fathers toasted freedom. Maybe shop for last-minute keepsakes and souvenirs to take home at Quincy Market or sample some local fare including Lobster Rolls, Clam Chowder, Fried Clams, Boston Baked Beans, followed by a slice of Boston Cream Pie.

Day Ten: Boston to UK

Check out of your hotel and transfer to the airport in time to board your flight back to the UK – hopefully with many happy memories to look back on of your Massachusetts by Rail adventure.

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