How to Spend 24 Hours In Pittsfield With Kids!

We Take a New Look At a Familiar Place

By Taylor Staubach, Publisher, Berkshires Macaroni Kid October 27, 2022

Nestled in the center of these famous hills and dales, Pittsfield is a historic little city, both vibrant and energizing. Staying overnight in Pittsfield places you in perfect walking proximity to a variety of restaurants and things to do. Plus, from here, everything else is just a short drive away, a huge bonus when you've got impatient kids in tow. We approached it as if we were visiting a “new-to-us” area, as if we had limited time (which we did) and so much to see.


Holiday Inn & Suites, 1 West St.

There's just something exciting about spending the night in a hotel and our time at the Holiday Inn really set a dramatic stage for our 24 hour trip. The view from our room on the 12th floor was absolutely stunning and transported us beyond our familiar city. With a comfy sofa bed all made-up and waiting, knowing that our beds were waiting for us less than a 10-minute drive away was a comforting feeling. Knowing that we didn’t have to make up the beds the next morning was even better. Our room also included a kitchenette, an extra-helpful feature for anyone traveling with kids. The highlight of our stay at the Holiday Inn was the pool! You'll find the heated indoor pool underneath a massive skylight — the kids were thrilled to go for a swim and once it got dark, the colorful lights made our night swim unforgettable!


Berkshire Museum, 39 South St. 

A quick walk across the street from the Holiday Inn, you'll find the historic Berkshire Museum. Not only does it house the Berkshires only aquarium, you'll have to tear your kids away from the Spark Creativity Lab if you want to see all there is to see at the museum — the Feigenbaum Hall of Innovation (with kid-friendly activities), theater, rotating exhibits, natural history (my favorite is the Berkshire Backyard!), and art and antiquity installations. Be sure to save enough time to visit Pahat the mummy, Wally, and Old Bill! 

Open Monday-Saturday, 10 a.m.-5 p.m., Sunday 12-5 p.m. 

Admission: $15, Adult; $8, Child Age 4 to 17; Children ages 3 and under visit free!

Have a Pittsfield Library card? Save even more on your staycation by reserving Museum passes and more. Click here to find out more.

Beacon Cinema, 57 North St.

As any caregiver knows, having an escape hatch or a plan b with kids is a necessity. When you’re playing tourist in your neighboring city, being close to home and familiar with our surroundings was the perfect safety net for the unpredictability of life. So when things didn't quite go to plan (hello, rain!), we were confident enough to pivot and figure out an alternative activity. With reclining, heated seats and concessions that offer beer & wine, if you need a place to catch a flick when plans go left, the Beacon is the spot. An easy walk from the hotel puts you in the vicinity of both the cinema and multiple eateries — plus, the matinee is $7! 

General Admission: $10; Child, $7 (11 and under); Senior, $7 (60 and over); Matinee, $7 (All shows starting before 5 p.m.)

Hancock Shaker Village, 1843 W. Housatonic St.
A quick 10-minute drive from the center of Pittsfield transports you back into a simpler time. We could have spent the entire day exploring Hancock Shaker Village, a 750-acre living-history museum, that boasts twenty historically authentic buildings, heirloom gardens, livestock barn and pastures, and 1-mile Farm & Forest Trail. A landmark destination of 750 acres, 20 historic Shaker buildings and over 22,000 Shaker artifacts. On the National Historic Register, it is the most comprehensively interpreted Shaker site in the world and the oldest working farm in the nation. In the Discovery Room, kids can learn about farming, dress like a Shaker, make a craft to bring home, and even try their hand at milking a cow (replica). During our visit, we got to try our hand at weaving! The sprawling grounds offer room to let loose and on-site hiking trails enabled us to loop another adventure into our day. Make sure to check out all the animals!

Open daily 10-5 through October 31st. Open Friday through Sunday 11-4 beginning November 4th.

Admission: $20, Adult; $8 Child Ages 13-17; Children ages 12 and under visit free!

If you venture further...

Naumkeag, 5 Prospect Hill Road, Stockbridge

Open seasonally, this Gilded-Age home is a step back in time and experience. Explore the 44-room Choate family “cottage” and Naumkeag gardens, including the famed Blue Steps, Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, and Chinese Garden. Depending on the time of your visit, grab tickets to the incredibly popular Tulip, Pumpkin or Winter Lights shows. Our plans for the Pumpkin Show were initially thwarted by the rain, however our tickets were honored for a different night and it was a truly spectacular experience! See website for current offerings.


101 Restaurant & Bar, located in Holiday Inn & Suites

With rain in the forecast, it was so nice to check into the hotel knowing that dinner was just an elevator-ride away. 101 is a new, family-run business on the second floor of the Holiday Inn in Pittsfield owned by the same restaurant group that runs Patrick's Pub across the street. Here you'll find something delightfully different. The Southern-inspired menu was full of dishes we couldn't wait to try, but the menu also included kid-friendly options. The smoky and flavorful shrimp and grits was the perfect comfort dish on a chilly night. Capped off with a perfectly-balanced Manhattan, I can see why the drink menu is a fan favorite as well. 

Otto’s Kitchen & Comfort, 95 East St., Pittsfield. 

Another walkable eatery, Otto's is the prime location if you're looking for a delicious way to fuel up for the day ahead. Full of hearty breakfast and lunch options, the locals know where to go for good coffee in a laid-back atmosphere. Under the big windows, we watched the city come alive as the kids happily tucked in to their chocolate chip pancake stacks. From here, we plotted out our stops for the day. With the Pittsfield Library across the street and the Berkshire Museum around the corner, we took our full bellies for a walk in the fresh air. 

Open Wednesday-Sunday, 8 a.m. to 2 p.m.

Crust Pizza, 505 East St. 

After spending 3 hours exploring the Berkshire Museum, we were in need of a refueling. Lucky for us, Pittsfield has a wide variety of places to grab a casual lunch. With kids, pizza is almost always a winning decision, and when the pizza place is right next door to delicious dessert? Talk about a win-win. Crust Pizza is more than just a spot for a quick slice. Here you'll find unique combinations made with the highest quality artisanal ingredients by the friendliest staff. Crust offers 2 gluten free options, as well as catering to other dietary restrictions. The laid-back atmosphere was a must with two hungry kids zooming around and owner Jim Cervone was on hand to welcome us (he even gave the kids a VIP tour of the dough room)! Crust also serves salads and offers beer and wine, including beer on tap!

Crust is open Tuesday-Sunday, 11 a.m. to 8 p.m., Ayelada Monday-Friday, 11 a.m. to 9 p.m., Saturday & Sunday 12 to 9 p.m.

Ayelada, 505 East St.

Armed with leftovers (yum, cold pizza!), we hopped next door for something sweet. At Ayelada, you'll find fresh, frozen yogurt homemade with ingredients that showcase local farms. With dairy-free and vegan options, the hardest part is choosing which toppings to take your dessert to the next level. Flavors at Ayelada are always rotating and creatively highlighting what's in season — apple cider donut anyone? My favorite is the lemon with lemon crunch topping. The kids always opt for gummy bears or chocolate chips and it makes them feel good to wield the power of choice in this small way. The staff here is always incredibly friendly (and patient!) as we take our time deliberating. Owner Lisa Cervone took our visit over the top by offering to snap the kids pictures for the famous Ayelada wall!

Ayelada is open Monday-Friday, 11 a.m. to 9 p.m. and Saturday-Sunday, 12 to 9 p.m.

District Kitchen & Bar, 40 West St. 

After a jam-packed day, for the last meal of our staycation we were looking for a place with comfortable seats and good eats. District Kitchen delivered on both counts in a gastropub-like atmosphere with an upscale vibe that felt welcoming to a family of four. I love the rotating selection of craft beer and the menu offerings of small, mid, and big plates made it a breeze to order a kid-approved dish. The food here is top-notch, with unique twists on American-style cooking. The shishito pepper appetizer is a favorite, but everything we tried afterwards quickly took top spot. The service is friendly and attentive. District is a very popular restaurant and those in the know, know that reservations are absolutely recommended if you don't want to wait.

Open seven days a week, after 4 p.m.


Farm, Forest & Shaker Trails at Hancock Shaker Village

If you still have time after you've explored the buildings and animals at Hancock, take your adventure further and hit some of the village’s trails. The Farm and Forest Trail is a one-mile, universally-accessible loop trail that takes hikers through expansive pasture and woodlands adjacent to the historic village. Keep an eye out along the trail,for interpretive signs that highlight some of the significance points of the beautifully historic area. 

The trail is open during the Village’s regular visitation hours and is included in general admission.

Click here for a family-focused trail review!

Canoe Meadows, 309 Holmes Road

A short drive away from downtown Pittsfield, Canoe Meadows is a perfect place to get out in nature. Hike the trails, take in a free program or tour the gardens located along the banks of the Housatonic River. 

Free; donations accepted.

Click here for a family-focused hike review. 

More Places to Get Outdoors...

Looking to explore the Berkshires in all its seasonal glory? Here are some more picks, all just a short drive from the hub of Pittsfield. 

Mahanna Cobble101 Dan Fox Drive

Is your family up for a challenge? The view is totally worth the climb! Pro tip: Stop at Lyft for a fuel-up before or after your hard work!

Arrowhead, 780 Holmes Road

Enjoy a house tour of the restored home of famed Moby Dick author Herman Melville (Admission Fee) or opt for a self-guided tour of the grounds (Free). Print off a copy of Stanwyk's Scavenger Hunt to engage everyone on the adventure!

Wild Acres, South Mountain Road

Located next to the airport off of South Mountain Road, Wild Acres is a great spot to take your kids hiking, fishing, and airplane watching. Click here for a family-focused trail review.

Pittsfield State Forest, 1041 Cascade St. 

With over 11,000-acres, Pittsfield State Forest is a massive playground for hikers, bikers, and adventurers alike. Highlights include the head-scratching and gravity defying Balance Rock, the vista and views from the top (you can drive up!), and the accessible Tranquility Trail. Daily parking fees May 14 - Labor Day: MA residents, $5; Non-MA residents, $20.

The BNRC Berkshire Trails app is a comprehensive guide to hiking trails in the area, including state forests, parks and nonprofit land preserves if alternatives are needed. 

Check out Berkshire Family Hikes for more family-focused local trail reviews

Our 24 hours in Pittsfield successfully broke up the monotony of the every day and brought the fun factor back into our lives. This staycation was the perfect way to disconnect from our daily routine and take a look at the place we live through a new lens. It enabled us to be a tourist in some of the most familiar place, and appreciate the fact that we didn't need to go far (or anywhere, really) to do so. 

I'm reminded of this quote by Charles M. Schultz, "In life, it’s not where you go, it’s who you travel with.” Our time in Pittsfield really embodied that message. We were able get away to unplug, rest, recharge, and re-connect with our sense of place, but most importantly, we were able to use that time as a family to connect with each other. 

*BIG thanks to the City of Pittsfield, MA for hosting our 24 hour staycation!