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Explore Unique Adventures Near Pittsfield

Unique Adventures Near Pittsfield - Retro Pop Shop
Camille Reddick
Camille Reddick
April 25, 2025

Looking for getaway ideas that are out of the ordinary? The Berkshires landscape offers many beautiful, fun attractions that will take you off the beaten path. If you spend a little time in Pittsfield, you'll have plenty of opportunities to explore amazing shops and gorgeous natural spaces. Here's a peek at five unique things to do near Pittsfield, MA.

1. Retro Pop Shop

You'll love this quirky shop with many collectables, antiques, and soda swag. As you browse an impressive collection of retro items and memorabilia, take your time. From neon signage to classic Coca-Cola vending machines, Retro Pop Shop takes you back to simpler days. The best part is that the shop is attached to a little stand serving up locally made ice cream.

Cidery Tours at Hilltop Orchards

2. Cidery Tours at Hilltop Orchards

Hilltop Orchards offers wine and cider tastings amid the backdrop of a stunning 100-year-old orchard. The property offers views of three states! When you come, plan to take a cidery tour, hike the grounds, and nibble on Hilltop's famed cider donuts! A cider tasting here offers the chance to taste a delicious artisanal cider made in a small batch. Hilltop Orchards is notably the home of the original Johnny Mash American Cider. Dogs are welcome!

Onota Boat Livery

3. Rent a Boat at Onota Boat Livery

Spend a day on Onota Lake in Pittsfield, MA! This gorgeous 617-acre lake is a favorite spot for boating and fishing! While you can enjoy the water from the shore or pier, there's something special about getting out on the water in your boat. This jewel of Massachusetts is home to a wide variety of fish, including largemouth and smallmouth bass, rainbow trout, yellow and white perch, black crappie, rock bass, and rainbow smelt.

4. Three Sisters Sanctuary

Get away from the world at this gorgeous art space that welcomes you to explore sculptures, gardens, and natural beauty. Designed as a space for meditation and contemplation, the sanctuary contains 25 different points of interest. Highlights include labyrinths, a pond, pollinator gardens, and a mosaic dragon. Three Sisters Sanctuary is open from 8 a.m. to 6 p.m. weekly.

Hancock Shaker Village

5. Hancock Shaker Village

Experience Pittsfield as it was at the historic Hancock Shaker Village. This living history museum features a working farm with livestock and poultry. Guests can also browse exhibits, visit art installations, dine at a seasonal kitchen, and shop at the mercantile. Hancock Shaker Village hosts fun holiday events and "animal" days yearly.

Enjoy the Unique Treasures of Pittsfield and Other Berkshires Towns

This is where art, history, and the simpler things in life come together for the sweetest getaway experience imaginable! Don't stop with unique things to do near Pittsfield, MA! The region is filled with quirky, fun museums and attractions. Just check out this list of unusual things to do in the Berkshires to get some inspiration for the rest of your trip!