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The Perfect Four-Day Massachusetts Road Trip For Art, History, and Culture

Massachusetts Road Trips Insider Guides
by JoAnna Niles Nov 30, 2023

As the seasons change, there’s no better time to escape the busy city life and take a road trip. The New England region has a rich history, culture, and natural beauty, making it an ideal destination for scenic drives. If you’re in the northeastern United States looking for an escape, here’s an extended weekend guide sharing the best places to visit on a road trip through Central and Western Massachusetts, including small towns, historical landmarks, mountainous terrain — all with a stunning backdrop.

When to do a Massachusetts Road Trip

If you’re interested in enjoying the warm weather and coastal areas, summer months are ideal. This time is perfect for for those who enjoy the outdoors. For some of the best fall foliage peeping in the US, late September to mid-October is the optimum time to catch the leaves at their most vibrant.

Day 1: Arrive in Northampton

View of the campus of Smith College, a private liberal arts women's college in Northampton, Massachusetts

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Start your road trip adventure in Northhampton, a town in the heart of Western Massachusetts. Throughout the year, Northampton hosts several events, such as the Chalk Art Festival and Arts Night Out, every second Friday of the month. These events celebrate the town’s cultural and art scene. If traveling from the New York City area, take the Amtrak from Penn Station to Northampton via the Vermonter. The scenic train ride will show a picturesque backdrop, setting the tone for your upcoming adventure as you capture views of the Northeast Corridor.

Hotel Northampton a stop on Massachusetts Road Trip

Photo: Joanna Niles

Check into Hotel Northampton, a hotel a short drive from the Amtrak station and within walking distance from Smith College. Hotel Northampton opened in 1927 and is known for its glass atrium, the Grand Ballroom, and notable past guests. With 14 distinct room types, you’ll find the perfect space to unwind at the start of your trip. Additionally, Hotel Northampton is a registered historic landmark, and the property has many photographs and artifacts from the original hotel, offering a glimpse into the past.

The hotel has two restaurants: The Coolidge Park Cafe, named after former President Calvin Coolidge, who served as the Mayor of Northampton and is open seven days a week, and Wiggins Tavern, a restored 18th-century tavern offering Sunday Brunch.

Hotel Northampton is close to many shops and popular restaurants in the area, including HighBrow Wood Fired Kitchen & Bar, known for its American cuisine with French and Italian influences, and Herrell’s Ice Cream and Bakery, founded by Steve Herrell, a business owner who popularized mixing candies, cookies, and other ingredients into ice cream.

Day 2: Explore Northampton, Florence, and Deerfield

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After breakfast at Hotel Northampton’s Coolidge Park Cafe, visit the Botanic Garden at Smith College, a 125-year-old garden free and open to the public year-round. The Church Exhibition Gallery, once a unique growing space, is an excellent starting point. The gardens are home to various plants from around the world and host multiple exhibitions and events throughout the year, including flower shows in November and March. Plus, you can explore the college’s rich history with notable alums such as Gloria Steinem, Julia Child, Nancy Reagan, and Sylvia Plath.

After exploring the Botanic Gardens, continue the cultural experience by visiting the Smith College Art Museum, which offers a range of contemporary and historic art collections. Admission is free, and the museum’s galleries rotate regularly. Smith College Art Museum is also well known for its two all-gendered bathrooms on the lower level, designed by artists Ellen Driscoll and Sandy Skoglund to represent functional art.

Stop for lunch at Paul and Elizabeth’s, a local restaurant that specializes in vegetarian and seafood dishes. The restaurant is in Thornes Marketplace, an old department store that has transformed into an indoor market. Today, the marketplace is an independent space with five floors of shops selling food, drinks, books, and clothing. Some highlights include Share Coffee, a local coffee shop offering freshly brewed coffee and pastries for a quick snack or a pick-me-up. And The Blue Marble a boutique selling clothing and handcrafted jewelry. It’s the perfect place to find a unique keepsake or gift for friends and family.

Fall foliage in the hills of Florence, Massachusetts a stop on a Massachusetts Road Trip

Photo: Emma’sPhotos/Shutterstock
Fall foliage in the hills of Florence.

Florence, a short distance from Northampton, is known for its association with the Underground Railroad. Several houses and landmarks in the area are designated for their historical significance, including the David Ruggles Center for History and Education, which honors David Ruggles and other participant’s contributions to the abolition of slavery in Massachusetts. There is also a memorial of Sojourner Truth, a formerly enslaved person, abolitionist, and activist who lived in Florence, in the mid-1800s.

 Yankee Candle Village in South Deerfield, a stop on a Massachusetts Road Trip

Photo: Joanna Niles

Continue your road trip to Yankee Candle Village in South Deerfield, about 15 minutes from Hotel Northampton and the number one tourist destination in the Pioneer Valley for over 10 years. Founded in 1983, Yankee Candle is a New England staple offering over 200 scents and home essentials. Discover the Candle Emporium, which includes options to create a jar candle or a candle bar experience mixing fragrances for a custom blend. The fall and holiday seasons are the busiest. Throughout the year, there are over 40 events, including Fall Fun Weekends, Holiday Open House, Santa’s Arrival, and more during the spring and summer. The variety of activities at Yankee Candle makes it a perfect destination for families.

Deerfield, Massachusetts

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Head north to take a trip to Historic Deerfield, which is the most southern town in Franklin County. Historic Deerfield is an outdoor museum of refurbished historic houses from the 18th century. General Admission to Historic Deerfield is $18 for adults, $5 for children 12-17, and free for children under 12, members, and residents of Deerfield and South Deerfield. In addition to providing daily tours of the historic houses, Historic Deerfield partnered with the Witness Stones Project, Inc., a Connecticut-based organization working to acknowledge and honor the men, women, and children enslaved in Historic Deerfield.

Visitors can stay overnight at the Deerfield Inn, a 24-room bed and breakfast located in the heart of Historic Deerfield. The property features Victorian-style decor with modern amenities, and a restaurant on site provides breakfast, lunch, and dinner using locally sourced ingredients.

A beautiful view of the autumn trees in Pioneer Valley, Massachusetts, New England, USA

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For panoramic views of the Connecticut River, the Pioneer Valley, the Pelham, and Berkshire Hills, drive up to Mount Sugarloaf State Reservation. This area has over 500 acres of parkland and is great for birding, hiking, road biking, and picnics. Admission for state residents is $5 and $20 for non-residents.

An alternative to staying in Deerfield is driving 30 minutes south to Springfield, and checking into the MGM Springfield, a 250-room boutique hotel and casino in Metro Center Springfield. This smoke-free property has over 1,500 slot machines and a poker room, offers table games, has a sports bar, restaurants, a movie theatre, a bowling alley, and includes entertainment for comedy and concert lovers. The hotel incorporates industrial elements that pay homage to the history of the city and partners with local artists and artisans in the Springfield, greater Berkshires, and New England areas in their art collection.

End the night with dinner at Latitude Restaurant in West Springfield, an American restaurant by Jeffrey Daigneau offering unique dishes and cocktails using farm-to-table ingredients. Some local favorites include Brussels sprouts, sweet chili aioli, braised beef short ribs, traditional Caesar salad with anchovy dressing, and caramel apple creme brulee.

Day 3: Springfield to Worcester

Springfield, Massachusetts, USA downtown skyline on the river at dusk. A stop on a Massachusetts Road Trip

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Springfield is also the birthplace of basketball, founded by James Naismith, a Canadian-American physical education coach at Springfield College, where the sport was created using two peach baskets attached to the walls as the original hoops.

The Naismith Memorial Basketball Hall of Fame

Photo: Joanna Niles

The Naismith Memorial Basketball Hall of Fame is an interactive museum celebrating the men and women coaches, professional and amateur players, and other contributors to the sport. Visitors can purchase passes from $18-27, and children under five are free.

A group shot of The Horton Court sculpture at the Dr. Seuss National Memorial Sculpture Garden

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A short drive from the Basketball Hall of Fame is the Springfield Museums, which consists of five museums covering art, history, and science, and the Dr. Seuss Museum and National Memorial Sculpture Garden. Admission includes access to all the museums, and costs $25 for adults, $16.50 for college students and seniors over 60, $13 for youth 3-17, and free for children under three and residents of Springfield.

Before your next destination, have lunch at Frigo Foods Springfield, a family deli serving Western Massachusetts since the 1950s specializing in gourmet sandwiches, gift baskets, and catering services. You can’t go wrong with one of their daily soup specials. If you’re in a large group, order one of their boxed lunches from the catering menu, which includes a beverage, salad, cookie, potato chips, utensils, and condiments.

Take an hour’s drive to Worcester and check into the Beechwood Hotel, the only AAA 4-Diamond hotel in Central Massachusetts. This pet-friendly property has 52 guestrooms, 21 suites, a restaurant, and a cocktail lounge. Minutes from downtown Worcester are attractions like the Hanover Theatre, Wormtown Brewery, Quinsigamond State Park for swimming, sailing, fishing, and Tower Hill Botanic Garden.

A short drive away in Groton, have dinner at Gibbet Hill Grill, located next to Gibbet Hill Farm, which produces fresh ingredients for chefs in the area, before catching a show at the new Groton Hill Music Center.

Day 4: Discover Worcester and Wachusett Mountain

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After breakfast at the Beechwood Hotel’s Sanoma Restaurant, head to the Salisbury Mansion. Salisbury Mansion is a restored 17-century former home and store of Stephen Salisbury and the only historic house in Worcester. Salisbury Mansion is also a short walk from the Worcester Art Museum, founded by Stephen Salisbury III in 1898.

The Worcester Art Museum serves as a teaching museum, engaging with the local community and fostering an appreciation for art and culture. Its mission is to allow visitors to see the world across the centuries, and the exhibits reflect this objective. The Jeppson Idea Lab also combines science and art, showcasing how various art pieces are preserved. Admission to the Worcester Art Museum is $18 for adults and free for college students and visitors under 18.

Beers at Worcester Public Market

Photo: Joanna Niles

Have lunch at the Worcester Public Market, an indoor marketplace offering various cuisines from the Caribbean, North America, and Asia, which mirrors the diversity of the city of Worcester. Drink one of the 24 beers, hard seltzers, margaritas, or non-alcoholic beverages from Wachusett Brew Yard. There are also select seasonal drafts, such as Octoberfest Ale and Pumpkin Ale.

Picnic table with a scenic view of Monadnock Mountain in Wachusett Mountain State Reservation a stop on a Massachusetts Road Trip

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Before heading home, end your Massachusetts road trip at Wachusett Mountain. The ski resort hosts several festivals and events, including Applefest, an annual event featuring local beer, food, craft vendors, live music, and entertainment for visitors of all ages. Take the ski lift to the top of Wachusett Mountain for scenic views as far as Boston on a clear day. After capturing breathtaking views, end your trip with apple cider donuts at a vendor booth from one of the local farms.

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