The Annual Middle Street Walk is a great way to experience Gloucester's Historic District and waterfront while having Holiday fun with the family. An updated schedule of this years walk will is available for download at this link.
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays. Go at your own pace and learn from interpreters stationed in rooms.
Enjoy freshly baked cookies and hot chocolate, try the Crane holiday eye spy, and shop in the Castle Hill Gift Shop during your visit.
Get ready for family fun every Friday night all summer long at Salisbury Beach! Starting at 7:15 PM on the Salisbury Beach stage, enjoy a full evening of summer tunes and excitement. DJ Ralphie B will be spinning your favorite hits, while hosting kid-friendly activities that will keep everyone entertained.
Main Street, Downtown Gloucester Massachusetts comes alive when the Street is closed off to allow live music, street performers, kid activities, non-profits, food vendors and more! Many of shops and businesses on Main Street will be open for business and will welcome partygoers. Other Gloucester businesses and non-profits will be represented on the Street as well. come for a night full of Live music, great food, and fun activities with lots of local flavor!
Ipswich Downtown Tuesdays includes great dining, live music, dancing at the Take-Out Terrace Stage on the Riverwalk & extended shopping hours for shopping Downtown Ipswich Tuesday evenings! Each week will feature live entertainment on the Riverwalk, making for a fun evening out for the whole family!
Come to Salisbury Beach every Tuesday, July through August for FREE seaside, family friendly activities! Starting July 11th, every Tuesday, thorugh August 22 there will be free family friendly programing at the Salisbury Beach Center.
Get ready to cheer on the incredible youth of our community at the 2025 Yankee Homecoming Kids Talent Show! This beloved family-friendly event returns to the Newburyport waterfront stage on Monday, July 28th, from 11 AM to 1 PM, bringing an exciting showcase of music, dance, magic, poetry, and more.
Come to Ipswich Massachusetts for the Annual Greek Festival: A 75-Year Tradition in Greater Boston and the North Shore! Experience one of the longest-running and most cherished traditions in Greater Boston, MA, and the North Shore area—the Greek Festival! For over 75 years, this event has been a beloved tradition for families and friends, both within the local Greek communities and beyond.
Marblehead, Massachusetts has a long-standing tradition of hosting an annual summer arts festival during the week of July 4th. This highly esteemed festival showcases a diverse range of artistic expressions that include: painting, drawing, sculpture, mixed media, printmaking, photography, crafts, plein aire painting, senior art, student art, and youth art. Alongside the art exhibits, there are numerous family-oriented festivities, events, and activities that aim to captivate and entertain both children and adults alike.
The Saint Peter's Fiesta is an annual festival in Gloucester, Massachusetts celebrating the city's fishing heritage, close-knit families, community, and religious traditions. The five-day celebration includes a carnival, live entertainment, and unique traditional events like the infamous 'Greasy Pole' contest and classic seine boat races. The festival is proudly sponsored by the Italian-American fishing community of Gloucester, and has all kinds of family-oriented activities and events, making it a great early Summer destination weekend event.
