Group Tour Itineraries in the Pioneer Valley

Itineraries that say, "You've Just Got to Go to the Pioneer Valley!"

With group tour favorites including the Naismith Memorial Basketball Hall of Fame, Six Flags New England, Yankee Candle Company, Dr. Seuss National Memorial and Springfield Museums at the Quadrangle, Historic Deerfield and nearby Old Sturbridge Village, the Pioneer Valley offers a host of itinerary options year round. Add seasonal events including the 17-day Big E, Bright Nights at Forest Park, Holyoke's St. Patrick's Day Parade, Brimfield antique shows, Paradise City arts festivals and agricultural fairs, and you'll see the hardest part is deciding what to choose to include.

Sample Itineraries

We've offered some sample itineraries here, and we're happy to help you design an itinerary that will be perfect for your group - just give Alicia Szenda, Director of Sales for the Greater Springfield Convention and Visitors Bureau, a call at 413-755-1346 or via email.

Here are a few sample itineraries for your group, showcasing some of the very best the Pioneer Valley has to offer! For the full itinerary, click on read more.


Pioneer Valley Burger Trail
Who doesn’t love a delicious juicy burger? With the best burger stops in Western Massachusetts, this is one trail you will want to cover start to finish!

Don’tcha Want a Doughnut Trail
Cider doughnuts are a harvest tradition during autumn in New England, so we built a trail around it! With some of the best doughnut spots in Western Massachusetts, you’ll be hungry for this fall favorite all year long! Don’t forget to pair with a hot apple cider too!

Love Local. Eat Local. Trail
Western Massachusetts is very well known for its diverse agricultural landscape. With so many fantastic restaurants utilizing the local farming community to serve up delicious menus, we wanted to make sure you enjoy the very best in homegrown foods while visiting the beautiful Pioneer Valley.

We all scream for Ice Cream Trail
Who doesn’t love ice cream?! No matter what season it is there are plenty ice cream spots to enjoy all year long. Adding a ton of local flare to communities all across Western Massachusetts; we have built a trail of some ice cream parlor favorites that you will not want to miss out on while visiting!

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Homegrown in the Pioneer Valley
While visiting the Pioneer Valley in Western Massachusetts it is always nice to scout out the local spots that residents love calling their own! These unique finds offer perfectly filled day trips!

Shop 'Til You Drop
If it's shopping your group is looking for, then look no further than the Pioneer Valley. From outlet shops and malls to quaint country stores - it can all be found here!

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Things To Do

The great outdoors: Adventures in the Pioneer Valley
Western Massachusetts is known for its incredible outdoor adventures! With plenty to choose from during your stay, we have outlined some of the best that the whole family will enjoy! Buckle up and have fun!

Getaway Golf Weekend (2 day)
Looking for something to do for a weekend away? How about a relaxing weekend on the course? With absolutely no shortage of scenic beauty, golfing in Western Massachusetts is always a good idea.

Arrive Curious. Leave Inspired. The Educational Itinerary
With a variety of one-of-a-kind attractions, and affordable admission rates, the historic museums and treasures found in Western Massachusetts are perfect for the whole family to explore. We suggest making a day of it and getting to know the area’s best in educational attractions.

Nearly free in the Pioneer Valley
If you’re looking to explore Western Massachusetts, it certainly doesn’t hurt to get the most out of your trip! With plenty to do and see that is free or nearly free, we wanted to make sure you enjoyed your trip every step of the way, without breaking the bank.

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A River Runs Through It: A Pioneer Valley Itinerary

Water and the power it creates has always had its place in history and it's no different here in the Pioneer Valley. From a water-powered mill to a cruise on the Connecticut River, this itinerary could turn out to be a little "wet & wild!"

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Literary Legacies: An Itinerary in the Pioneer Valley

This literary trail will take you all over the Pioneer Valley, from poetry to picture book art and everywhere in between. You'll explore many wonderful homes, galleries and museums dedicated to the likes of Emily Dickinson, Mark Twain, and Dr. Seuss, just to name a few!

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A Nature Tour: A Pioneer Valley Itinerary

Mother Nature put her special touch on this itinerary! With breathtaking river views, exquisite butterflies, Victorian parks, and a little tasty treat... you'll want to take this tour spring, summer and fall!

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Riding High: A Pioneer Valley Itinerary

Whether you are blocking a jump shot from a famous NBA player, soaring through the clouds in a WWII fighter plane, or trying your luck at the roulette tables... you'll be sure to feel the excitement that this itinerary brings!

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