Summer Bucket List & Reader Recommendations for Western MA

The Cummington Fair is a gem of an agricultural fair that happens every August in the heart of the Hilltowns. Mark Melhorn, Arjuna Greist and Piet Slaghekke all picked “The Biggest and Best Little Fair in the Country” for our Summer Bucket List! (Photo credit: Sienna Wildfield)

With it’s natural beauty, local food, family attractions and community festivals and fairs, Western Massachusetts is a haven for family fun. Whether you’re visiting the area, or are fortunate enough to live here year round, the region in the summer is an engaging place to vacation or staycation! We asked our readers to recommend their favorite attractions, day trips, must see or must do family activities, and we received 75 great tips. While not an exhaustive list (nor in any order) of the fun and adventure 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.

1. “The (free!) spray park at the Beachgrounds Park in South Hadley.” — Sandra Dias (Holyoke, MA)
2. “We love to go blueberry picking at [Sobieski’s] River Valley Farm in Whately!” — Laura Muller (Amherst, MA)
3. “I like to pick up sandwiches and Polish treats from BBA Deli Market in South Deerfield, then hike up Mount Sugarloaf State Reservation for a picnic with a view.” — April Genung (Sunderland, MA)
4. “Musante Beach is a relaxing and inexpensive way to spend the afternoons reading, swimming and picnicking.” — Keith Lepine (Northampton, MA)
5. “I love to take a picnic to Greenfield Energy Park with my daughter and enjoy the music. She loves the music, play structure, and trains. Buckland Recreation also has movies out by the pool at night during the summer. Next best thing to the old drive-ins! (Northfield Drive-In is also a great summer activity….)” — H Loomis
6. “We love to go to Chapel Brook; a beautiful land near Ashfield protected by the Trustees of the Reservation. On one side of the road there’s is a lovely hike where beginning rock climbers can practice their skills. On the other side of the road is a series of cascading waterfalls, one even safe & gentle enough to slide down (with caution!). The water is deliciously icy-cold even on the warmest of summer days.” — Christy Winslow (Northampton, MA)
7. “Mass MoCA combined with Natural Bridge State Park (North Adams, MA) is always a good day trip. More locally, the Mill River offers countless great spots to bath–many of which are along our excellent bike paths.” — Ruth von Goeler (Northampton, MA)
8. “Frisbee in Child’s Park in Northampton. This park seems to be the most under utilized resource in the area. This well manicured gem harkens back to another time.” — Glenn Sullivan (Holyoke, MA)
9. “Walking on the Quabbin Dam (Belchertown, MA). It is a great place to take pictures of the kids.” — Matthew Galman (Shutesbury, MA)
10. “The Eric Carle Museum (Amherst, MA) is a great place to spend some time.” — Eugenie Wu (Shutesbury, MA)
11. “Any way you can float down the Deerfield River. It is sheer joy. It’s great 3 seasons, but late spring is very special – beautiful and exciting!” — Laurie Goddard
12. “The Upper Valley Music Festival in Turners Falls. It’s a noon to midnight event that takes place at multiple venues (including Great Hall at Great Falls Discovery Center) in downtown Turners. Celtic music, singer-songwriters, rock n’ roll, contra dancing, you name it. The days events (including lots of opportunities to dance) are family friendly. And all proceeds benefits the American Cancer Society to boot. Check it out. ” — Chris Scanlon
13. “Our favorite event is Yankee Doodle Days in Charlemont they have great fireworks and a demo Derby! Favorite everyday activities are the bike trails (i.e. Norwottuck and the Turners Falls one)” — Jen Knight (Bernardston, MA)
14. “We always make sure to go to the 3 County Fairgrounds (Northampton, MA) to catch a horse show, preferably the sliders – it is truly amazing.” — Heather Polson (Northampton, MA)
15. “Visit the Peace Pagoda in Leverett.” — Marion Hohn (Amherst, MA)
16. “Conway Station. Hike in and swim in that crystal clear water!” —Marissa Potter (Shelburne Falls, MA)
17. “We love to go to the Heath Fair! It’s the perfect family day trip. Be sure to watch the herding dogs, eat lots of good food and jump into the cross cut saw competition!!” — Zoe Johnson (Ashfield, MA)
18. “I second the Jacob’s Pillow Inside/Out stage. Also weekends at Camp Norwich (Huntington, MA) for members of the Northampton YMCA.” — Amy Meltzer (Northamtpon, MA)
19. “Summer isn’t complete without canoeing or kayaking (lots of places, but especially the DAR during blueberry season), blueberry picking at Fox Run, a summer hike at Graves Farms, soft serve from Village Green Greenhouse and Ice Cream (Williamsburg, MA) . . .” — Sara Barry (Haydenville, MA)
20. “We would go to Puffer’s Pond (Amherst, MA) every day if we could!” — Karen Bayne (Northampton, MA)
21. “On of our favorite summertime activities is playing Poohsticks on the bridge at the Mill River Recreation Area, and then walking on the trail to the Puffer’s waterfall.” —Melissa Miller (Amherst, MA)
22. “Swimming at Ashfield Lake and then eating on the deck at the Ashfield Lake House!” — Rona Leventhal
23. “Hot summer days mean heading to Flayvors of Cook Farm in Hadley for great ice cream and finding a spot to fish on a local river and if it has a rope swing~ bonus!” —Glenda Datsko (Greenfield, MA)
24. “The Cummington Fair in late August is fun for the whole family.” — Arjuna Greist (Greenfield, MA) 
25. “Since it’s so hot, I am reminded that one of our family’s favorite little trips is to Conway Station for a dip in that COLD water – so refreshing, so beautiful!” — Jessica Day (Greenfield, MA)
26. “Turners Falls Block Party is always a blast with excellent music, food and vendors. Any summer night in Northampton you can wander with a coffee or your favorite drink from any number of cafes, eat outside at a number of restaurants and enjoy street musicians. A hike or drive up Mount Sugarloaf State Reservation for beautiful views of this wonderful valley of ours. And of course the Green River Music Festival and the balloon lift-off on that Saturday morning are fabulous!” — Jeanne Baj
27. “The Cummington Fair was great when the kids were younger. Now we do a lot of fishing at Lake Metacomet in Belchertown.” — Mark Melhorn (South Hadley,  MA)
28. “We love to spend the day on the shores of the Westfield River. We bring a cooler of food and drinks and plan on leaving after bedtime.” — Elaine Randall (Lee, MA)
29. “My grandsons love the train and mini golf at Look Park in Florence.” —Ellen Greist (Hamden, CT)
30. “Enjoying good, local food at good, local restaurants outdoors when the air is warm and the breeze is gentle makes the living easy in summertime. Fortunately for all of us, there is an abundance of all of these in summer in Western MA. My favorites include the Lady Killigrew at the Bookmill in Montague and Mama Iguana’s in Northampton. We’re also fortunate to live amidst a number of local “creamies” and “frosties.” We’re big fans of the 5Js in South Deerfield (which also has super-sweet pick-your-own strawberries), and the Sugarloaf Frostie in Sunderland when it’s a hot-enough-for-ice-cream evening.” — Cheri Karbon (Deerfield, MA)
31. “Magic Wings Butterfly Conservatory & Gardens in Deerfield reminds me of home in Costa Rica!” —Sandra Salazar (Monteverde, CR/Hamden, CT)
32. “Fishing at the Highland Park Pond in Greenfield is free for kids under 12 and their accompanying adults. Bring kids, dogs, and bread/Cheerios to feed to the trumpeter swans along the canal in Turners Falls.” —Trystan Dean (Greenfield, MA)
33. “Best summer fun – Look Park! So much to do; all in one place! Of course the Taste of Amherst was fun (and yummy) too!” — Amanda Saklad (Belchertown, MA)
34. “Look Park is always one of our favorite places to go for a picnic, some water fun, and of course a ride on the train!!” — Dawn Kempf (Greenfield, MA)
35. “Mellow day and picnic at Lake Wyola State Park (Shutesbury) or Laurel Lake (Warwick). Hiking up Mt. Toby (Sunderland). Or a drive and hike to Lake Pisgah (Kilburn Pond in Pisgah State Park) in New Hampshire, picking wild blueberries while swimming!” — Siri Om Fuller (Leverett, MA)
36. “Free performances and Family Day at Jacob’s Pillow in Becket! Bring a picnic!” — Deanna Scarfe (West Chesterfield, MA)
37. “Frog hunting with my kids! We also love to visit a swimming pool in Williamstown, MA called Springs which uses fresh water from local springs to fill its pools. Look Park is also a favorite with its train rides and splash area.” — Matt Rich (Deerfield, MA)
38. “We love all the different swimming holes in the area! We try to hit up a bunch of different ones all summer long. Some are well known (Puffer’s Pond in Amherst) and other’s are local secrets.” — Avital Norman Nathman (Northampton, MA)
39. “Drive-in movies are always fun!” — Emily E. Murphy (South Hadley, MA)
40. “Mount Sugarloaf State Reservation (South Deerfield) at sunset.” — John Snyder (Sunderland, MA)
41. “Our absolute favorite thing to do is visit our local CSA- Natural Roots in Conway- or as my son likes to call it, ‘the food farm.'” — Katherine Golub
42. “Blueberry picking is a “have to” summer activity in Western MA- we love Bird Haven in Southampton. Also, The Wagon Wheel in Gill is a great local drive-in. If you’re looking for a fun ice cream experience and a scenic country drive, this is a good stop on Rt. 2.” — Anne Schlereth
43. “Mount Sugarloaf State Reservation (South Deerfield) f for a picnic and the view!” — Kimberly Jones (Westhampton, MA)
44. “Oh, the local swimming holes! Fav’s are Chesterfield Gorge (West Chesterfield), Plainfield Pond and waterfalls in Montague.” —Anneliese Mordhorst (Chesterfield, MA)
45. “Pick your own farms. Strawberries, blueberries, anything and everything!! There are so many great farms to choose from in our rich valley.” — Samantha Burnell (Williamsburg, MA)
46. “We love going to the Meekins Library (Williamsburg). They have great books/videos and free museum passes.” — Helene Leue (Ashfield, MA)
47. “The kids music scene is great.” —Jessica Morris (Northampton, MA)
48. “We enjoy walks through Arcadia Wildlife Sanctuary (Easthampton).” — Myssie Casinghino (Easthampton, MA)
49. “Berry picking at Summit Farm in Plainfield, MA.” — Dave Cahn (Cummington, MA)
50. “The Summit House (Skinner State Park in Hadley) is always a great spot for a hike and picnic during the summer. The views are spectacular.” — Chris Curtis (South Hadley, MA)
51. “The Shelburne Falls Trolley Museum is a local gem. You can ride the trolley all day long and try out the pump car!” — Kate Gerrity
52. “We enjoy the Cummington Fair.” — Piet Slaghekke (Easthampton, MA)
53. “We really enjoyed the Mutton and Mead Festival.” — Jessica Larkin (Bernardston, MA)
54. “Thursday night music at Greenfield Energy Park.” — Karen Wessinger (Greenfield, MA)
55. “Summer church fairs and festivals. I try to get to the church fair / arts fest in Worthington (Hilltown Arts Alive Festival). Its a mile of continuing fun and things to do.” — Catherine Salisbury (Plainville, MA)
56. “Camping at the Falcon Ridge Folk Fest just over the MA/NY border by Great Barrington – with family stage and activities for kids running full-tilt all weekend. A perfect never-miss summer activity for toddlers and tykes alike. Our nine and seven year olds look forward to this all year; they’ve been going since their pre-natal days!” —Joshua Farber (Monson, MA)
57. “Picnic dinner at the DAR in Goshen, followed by an evening canoe tour of the lake. The perfect after-work/after-camp end to a summer day.” — Jennifer Grow (Florence, MA)
58. “Besides the Green River Fest, I think my summer recommendation would be to enjoy the free Thursday evening concerts at Energy Park in Greenfield. Very family friendly!” — Judy Bennett (Greenfield, MA)
59. “So many fun places to visit…Natural Bridge State Park in North Adams, Look Park   (Florence), Ice Glen in Stockbridge, Pleasant Valley Sanctuary in Lenox, PIttsfield State Forest, Quassy Amusement Park in Connecticut.” — Terri Thorne
60. “We love the FREE Water Ski Shows across from the Oxbow Marina (Northampton)- every Friday night in June & July – The Oxbow Water Ski Show Team does a great job!” — Judy Bardwell (Deerfield, MA)
61. “I love taking the family to RI every year. We go camping at Burlingame State Park. It is affordable and about 4 mile to the beach. You can go hiking, swimming and canoeing…you name it; and the Westerly town beach has movie nights as well. There is so much to do, never enough time and very relaxing.” — Rebecca Wozniak Freitag (Haydenville, MA)
62. “One of our favorite places is Chapel Falls (Ashfield) for a hike then a dip in the falls to cool off!” — Eileen Hamel
63. “The DAR (Goshen) and Look Park (Florence) are great places to go in the summer. So much fun for the kids and parents too!” — Jennifer Gonyer (Williamsburg, MA)
64. “Nearby: I like high places. Poet’s Seat Tower in Greenfield and Mount Sugarloaf in Deerfield are good places to bring a picnic and see the scope of the Valley, but the Summit House is still first among equals for its look at the river and the hills… A little farther away: Gotta have some ocean on the perfect daytrip, and I still haven’t found a nicer beach in New England than Footbridge Beach in Ogunquit, ME. Take it from someone who grew up going to great New Jersey beaches. Don’t know why anyone would hassle with the Cape when you could go here.” — Don St. John (Amherst, MA)
65. “Robinson State Park in Agawam is a nice family place to picnic, grill and cool off in the water!” — Christa Figueroa (Holyoke, MA)
66. “I like to check out the dinosaur tracks off of Rte. 5 in Holyoke. It is near the entrance to Mountain Park. There is a path that leads you there.” — Deborah Hoppe (Russell, MA)
67. “We enjoy packing a picnic lunch and heading off to any of our local swimming holes for a refreshing dip….such as Musante Beach in Leeds or the DAR in Goshen!” — Amy Quinn (Leeds, MA)
68. Our fave daytrips; the (semi) hidden waterfalls of western Mass! Tannery, Bash Bish, Glendale, Chapel, just to name a few…” — Kara Kitchen (Plainfield, MA)
69. “We LOVE Old Deerfield–it has so many special events going on.” — Nancy Wood
70. “We love the Trolley Museum in Shelburne Falls. Especially the hand pump car.” — J. Engel
71. “We love Shelburne Falls! Potholes, Bridge of Flowers, McCuskers!” — Sue Overstreet
72. “We like hiking to the summit of Mt. Toby in Sunderland. Enjoying the view from the top of the firetower is always a treat .” — Eugenie (Shutesbury, MA)
73. “A nice day trip to Williamstown always hits the spot for my family. Visit Cricket Creek Farm, stroll Williams College and hit up the Bridge of Flowers (Shelburne Falls) on your ride there.” — Gabe Reif (Amherst, MA)
74. “Lake Metacomet in Belchertown has great fishing for families and one of the most relaxing atmospheres around. It’s a great place to go on quiet days. The Cummington Fair used to be really fun as well when the family was younger, but we haven’t been in a few years.” — Jonathan Melhorn (South Hadley, MA)
75. “My family is looking forward to picking blueberries at Quonquont Farm (Whately), then returning for peaches and apples. It is a beautiful location, delicious produce we select and lots of fun!” — Jessica Larkin (Bernardston, MA)
76. “Unity Park in Turners Falls is great. Modern playground with unique features and a water spray whale, it’s also next to an easy-going 3.6 mile long bike path along the canal. Picnic spots with tables and charcoal grills along the river, Unity park has a volleyball court, a baseball field and basketball court too. Fantastic SKATE PARK too. Follow the bike path to the free Great Falls Discovery Center and top it off with an ice cream right across the street.” — Christina Sheppard

Our friend Alli, over at Mom Smart Not Hard, has also compiled a list of 25 playgrounds, museums, swimming holes, outdoor activities, and indoor activities for you and your baby or toddler to enjoy throughout the seasons in Western MA. Check out Alli and her partner Trina’s website, which is a place dedicated to the journey through motherhood, from bump to baby.

If you didn’t see your favorite summer spot on the list, share it with the Hilltown Families community by sending us a message here:

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