Hilltown Families 
30 Autumn Suggestions: Things to Do & Places to See in Western MA
Autumn Bucket List
Reader Recommendations for Western MA
“The Ashfield Fall Festival is one of the most memorable small town events in the Pioneer Valley. Arrive early and have pancakes and strong coffee at Elmer’s, then step out and enjoy all that the town has to offer.” – Ken Johnston (Photo credit: Sienna Wildfield)
Western Massachusetts is a glorious region to explore with family and friends in the fall as the leaves start to change and drop, and harvest festivals and seasonal traditions happen each weekend. Whether you’re visiting the area, or are fortunate enough to live here year round, Western MA in the fall is one of the most beautiful places to be! We asked our readers to recommend their favorite attractions, must see or must do family activities during the fall, and we received thirty great tips. While not an exhaustive list (nor in any order) of the fun adventures families can have in Western MA, it’s a great place to start. If you have a recommendation to add to this list, please do! Post your suggestion below.
- “One of my favorite fall destinations in Western MA is the Berkshire Botanical Garden Harvest Festival in October. Lots of things to see and do for both adults and kids…food, crafts, games, white elephant and book sales…not to mention the gardens themselves! Very affordable too!” – Rosy Crittendon (Otis, MA)
- “Go to Atkins Farms (Amherst) and get fresh hot apple cider and a bag of cider donuts. Eat a few donuts while sipping your hot cider, then hike to the top of Skinner Mountain and enjoy the rest of the bag as your reward.” – Shannon Dillard (Holyoke, MA)
- “We love the Berkshire Coaching Weekend. It is held every other year over Columbus Day weekend, falling on the even years. They have carriage drives to the Norman Rockwell Museum, The Mount, and Shakespeare & Co. It is free to go and watch them arrive or depart. Then you can walk among the carriages and ask questions. It is quite spectacular!” – Gretchen Fairfield (Lenox Dale, MA)
- “The Basketball Hall of Fame (Springfield) is a great rainy-day trip for the family and kids. Head to Coldstone Creamery in the same complex for a cool treat.” – Mary Rarogiewicz (Springfield, MA)
- “Franklin County Pumpkinfest!” – Marya LaRoche (Cheshire, MA) – (The Great Falls Festival – formerly known as Pumpkinfest)
- “My favorite family autumn attraction is to visit Outlook Farm on Rte. 66 in Westhampton! They offer apple picking, hay rides with horses, BBQ, ice cream, cider, pumpkins and even live music! They sell their own fruits and vegetables, and offer a wide selection of pork products. Their pulled pork, bacon, ham and sausage are outta this world! It really is a fun-filled day my family and I have enjoyed for years.” -Risa Mantino (Lunenburg, MA)
- “Lakeview Orchards in Lanesboro. Apple picking, hayrides, and warm apple cider donuts. Along with great views.” – Kenna Major (Adams, MA)
- “Apple picking at Pine Hill Orchards (Colrain), then baking pies with the kids.” – Victoria Lenois (Colrain, MA)
- “Definitely the Big E (West Springfield)!! Best fair of all time. Enjoy a main baked potato followed by a cup of hot apple cider. I would also recommend going to pick some pumpkins and enjoy some cider donuts at Atkins Farms (Amherst).” – Kristen Frodema
- “Okay, fall time is to have fun, so Mike’s Corn Maze first in Sunderland, then off to Long Hollow Bison Farm in Hadley. How about dinner at the Goten of Japan (Sunderland) where they cook the food in front of you?” – Pamela Brown
- “Get a lunch to go from Tail Gate in South Hadley and bring with you to eat after a hike at MT. Tom Reservation. Or go to Skinner Mountain, take a look at the scenery, and eat your lunch on the rocks on top of the mountain and take in the view. Absolutely amazing. End your day by going to Atkins Farms (Amherst) for cider doughnuts and cider.” – Megan Brunelle (Holyoke, MA)
- “Leaf peeping as we ride to Hilltop Orchard (Richmond) to go apple picking, hayride, cider donuts and apple cider. Mom and Dad get a bottle of wine to take home for the holidays.” – Lorna (Wilbraham, MA)
- “Taking a leaf-peeping drive through The Quabbin…” – Jennifer Meighan (Belchertown, MA)
- “I recommend taking a ride to South Deerfield to Yankee Candle and then go down the road to Magic Wings Butterfly Conservatory & Gardens. Not only will you be visiting two amazing places, but you’ll also be able to enjoy the breathtaking foliage!!!” – Sue Messier
- “I enjoy taking my family to Whitney’s Farm pumpkin patch (Cheshire)! They have an amazing assortment of fall activities including haunted hay maze, pony rides, giant slide and of course pumpkin picking! My kids favorite time of year!” – Jennifer Carchedi (Pittsfield, MA)
- “The Ashfield Fall Festival is one of the most memorable small town events in the Pioneer Valley. Arrive early and have pancakes and strong coffee at Elmer’s, then step out and enjoy all that the town has to offer.” – Ken Johnston
- “Randall’s Farm (Ludlow) corn maze, pumpkin decorating, scarecrow contest and fall festival.” – Carmela Smith (Palmer, MA)
- “The Apple Festival at Outlook Farm in Westhampton! Apples, hay rides, music and food! Reminds me of the apple festivals we used to go to back in my hometown in Michigan!” – Lisa Zacks (Williamsburg, MA)
- “Quonquont Farm in Whately for apple-picking. A beautiful location and a wide variety of apples.” – Diane Zamer (Florence, MA)
- “Enjoy Mount Greylock (Adams) with a picnic lunch and view the spectacular scenery of foliage. Kids love climbing up to the top of the memorial to take pictures.Tons of hiking trails. The lodge has some yummy ice cream treats inside! Last but not least huge bonus they have clean bathrooms!” – Rhianna Burke (Pittsfield, MA)
- “Go for a bike ride on the bike trail in Northampton, stopping for ice cream before you leave.” – Lori Reese
- “The Belchertown Fair is always a great family fall event.” – Chris Curtis (South Hadley, MA)
- “The North Quabbin Garlic and Arts Festival!” – Jessica Larkin (Bernardston, MA)
- “We went to Hilltop Orchard in Richmond, it was a wonderful time, we took a hayride out to pick the apples and got a hayride back. Then the next day we baked, and of course a fire in the fireplace is a fall favorite for our family.” – Tiffany Kingsley (Lee, MA)
- “Hiking on the top of Mount Greylock and lunch at the Bascom Lodge (Lanesborough)! Lovely in the Fall.” – Tina Cornell (West Chesterfield, MA)
- “In late November our favorite family tradition is Moonlight Magic in the village of Shelbune Falls the Friday after Thanksgiving, and the Gorge Apres Gorge annual family walk/run at the Chesterfield Gorge in West Chesterfield the Sunday also after Thanksgiving.” – Sienna Wildfield (West Chesterfield, MA)
- “I’d like to hike the many trails I’ve never hiked that I didn’t hike this summer because it was just too hot!” – Valerie A. Sheehan (Lenox, MA)
- “My family loves Hilltop Orchard in Richmond for apple picking- nice views and super yummy donuts and pies.” – Oriana Falkowski (Haydenville, MA)
- “Ashfield Fall Festival” – Jessica Thompson (Ashfield, MA)
- “To start the day off right head to Mike’s Corn Maze (Sunderland), then head over to Yankee Candle (South Deerfield) to dip your own candles. From there, swing by Magic Wings Butterfly Conservatory & Gardens, then head down to the Big E (West Springfield) for a baked potato. If closer to December try heading out to Bright Nights (Springfield) for a winter wonderland of lights before heading home.” – Karen Addie (Enfield, CT)
Northampton’s Historic Laurel Park is hosting a day-long fall Chautauqua festival on October 14th entitled “A Celebration of Trees”. Kick off is Friday night around the Friendship Fireplace with tree stories and poems, facilitated by Sabrina Hamilton, director of Ko Festival. Saturday events start at 10:00 with a guided walk through Laurel Park’s nine acre woods with naturalist Laurie Sanders, followed by a panel on the subject of conservation, preservation, and forest health. Children’s activities will be ongoing throughout the day, with tree-themed movement led by Duncan dancer Laura Pravitz. Other events include presentations by New England Apple Association author Russell Steven entitled “The Eternal Struggle to Tame the Wild Apple Tree”, with apple tastings and award-winning apple pie for purchase; a woodworking talk entitled “Seeing Figures in Wood: Tree-themed sculpture and photography exhibit; . All events are free. Lunch of soups and bread are served at a nominal fee.
Promises to be a wonderful celebration honoring our local trees.
Go to laurelparkarts.org for details.
Looking for a place that is a nice ride from springfield mass to pick pumpkins do a core maze have something to eat and other activities
Again no one mentions the huge fall foliage festival in North Adams. Many different events including a big parade.
Don’t forget Lee’s Founder’s Day’s… with parade and town activities all day, starting with Taste of Lee … and Lenox’s Apple Squeeze the following weekend …
Ashfield Fall Festival-Boy scouts make cider donuts that are the best in the entire world…also First Cong. Church soups are awesome…great yardsales and kid made and operated games on the common…
Generally getting out into the woods and hills.to see the foliage -we are SOOO lucky to have such glory in our midst in all of these hilltowns :)
Garlic and Arts in Orange is one of the best festivals ever…so diverse and deep-really exposing higher level thinking, lifestyle and creativity…
Conway’s annual Festival of the Hills. Not to be missed. Where else can you take in the Skillet Toss?
Our family always goes to the Hatfield Fall Festival. For kids, there’s face painting, Balloon Man, cider pressing, pumpkins and antique tractors and trucks to look at. For older “kids,” there are weaving, spinning and rug making demos, awesome antique cars, a library book sale, and both museums open at the same time (all free).And don’t miss the Hatfield fries cooked up with local potatoes by the Boy Scouts and a bargain-priced farmers market. This year they’re doing a demo on how to make sauerkraut, so you can buy cheap cabbages and go right home to make your own!