Pittsfield
Day Trips
Make the most of your day with our curated plans, packed with Pittsfield's hidden gems and unique experiences!
Start your day at the Berkshire Museum to explore local art and history. Enjoy a coffee break at a nearby café afterward.
Visit the lively downtown area for shopping and lunch at a local eatery. Check out the displays at the Shire City Sanctuary.
Catch a performance at the Barrington Stage Company for some great local theater. Wrap up with a delightful dinner at a restaurant downtown.
Begin with a refreshing walk at Lake Onota, surrounded by beautiful scenery. Consider bringing a picnic breakfast to enjoy by the water.
Explore the trails at Pittsfield State Forest for a mid-day hike. Take your time to appreciate the wildlife and natural beauty.
Head back into town and dine at a local grill. After dinner, take a stroll through the park to enjoy the sunset.
Visit the Norman Rockwell Museum to admire the iconic artwork. Enjoy a guided tour to enhance your experience.
Stop by the Berkshire Athenaeum, the town’s public library, for literary exhibits. Grab lunch at a nearby café featuring local ingredients.
Wrap up your day with a lovely dinner at a restaurant with a view.
Start your day at the Pittsfield Historical Society to learn about the city's rich past. Participate in a guided tour to make the most of your visit.
Head to Arrowhead, the home of Herman Melville, for more historical insights. Enjoy a packed lunch in the beautiful garden.
Wrap up your evening with a nightcap at a cozy bar.
Rent a bike and explore the scenic Ashuwillticook Rail Trail. Stop for brunch at a diner along the way.
Continue cycling to Berkleigh Park for some fun and relaxation. Bring along a frisbee or games to enjoy in the park.
Conclude your adventure with a casual dinner at a burger joint. Share stories of your day's excitement with fellow travelers.
Begin with a visit to the Berkshire Carousel to enjoy a whimsical ride. Kids will love the colorful horses while parents appreciate the craftsmanship.
Spend time at the fun-filled Bousquet Mountain for a day of outdoor activities. Enjoy a packed lunch at one of the scenic spots.
Enjoy a family dinner at a kid-friendly restaurant. End the day with ice cream from a local creamery.
Start with a yoga class at a local studio for a calming start. Follow it up with a healthy breakfast at a nearby smoothie bar.
Indulge in a spa treatment, making sure to relax completely. A light lunch at a health-conscious café would be perfect after your pampering.
Enjoy a quiet dinner in a cozy bistro. Wind down the day with a good book or a movie at home.
Join a guided food tour to sample local delicacies. This will give you an excellent overview of Pittsfield's culinary scene.
Visit various eateries focusing on farm-to-table dining experiences. Lunch can feature seasonal dishes created by local chefs.
Wrap up with dessert from a local chocolatier.
Participate in a local festival, where you can enjoy arts and crafts. Grab breakfast from food vendors to fuel your day.
Join in activities like live music, dance performances, and workshops. Sampling different foods can be a delightful adventure.
Continue enjoying the festival with a concert or community gathering. Celebrate the evening with friends and family under the stars.
Start your day at the Pittsfield Farmers Market to enjoy fresh produce. Sample local baked goods and specialties.
Wander through unique shops in the downtown area. Enjoy lunch at a local deli with freshly made sandwiches.
Visit a local bookstore for an evening book signing event. Wrap up the day with a cozy dinner at a charming restaurant.