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Ipswich Illumination 2023

The annual Ipswich Illumination festival returns this October, bringing art exhibits, performances, vendors, and live music to downtown Ipswich. The floating bonfires are the highlight of the weekend—on Friday, October 6, from 6 p.m. to 9 p.m., head to the Riverwalk to see ethereal bonfires float down the Ipswich River. Other happenings that weekend include […]

Appleton Farms Oktoberfest 2023

Appleton Farms 219 County Road, Hamilton & Ipswich, Massachusetts, United States

Practice holding a stein for Oktoberfest at Appleton Farms on October 14 and 15. The weekend-long festival will feature German-inspired food, lawn games, traditional German Hammerschlagen, and live music from oompah band Wunder Kapelle. Local breweries Notch Brewing, Essex County Brewing Company, True North Ale Company, Far From the Tree Cider, and 1634 Meadery will […]

Castle Hill Vintage Car Climb 2023

Castle Hill on the Crane Estate 290 Argilla Road, Ipswich, United States

The Trustees have partnered with the Vintage Sports Car Club of America for the return of the Vintage Car Climb. Pre-WWII cars will compete in timed races up Castle Hill’s roads and will be displayed in the Great House’s forecourt during the midday break. Guests can also expect live music, food from onsite vendors like […]

Sweet Halloween at Cider Hill Farm

On Saturday, October 21, and Sunday, October 22, head to Cider Hill Farm in Amesbury for its Sweet Halloween, a fun (not spooky) celebration geared toward young kids. Make sure you come in costume and ready to trick-or-treat for sweets from the costumed farm staff throughout the property—they’ll even have a costume contest! And as […]

Smolak Farms Fall Festival Weekends

Smolak Farms 315 South Bradford Street, North Andover, Massachusetts, United States

Oct. 1–29Every Saturday and Sunday in October, head to Smolak Farms in North Andover for a day of apple picking, live music, lawn games, hay rides, or just hanging out at their outdoor wine and beer bar. They’ll have face painting, crafts, and an animal playground area for the kids, too. Their beer bar features […]

Sweet Paws Rescue’s Barktoberfest Fundraiser

Spencer-Peirce-Little Farm 5 Little’s Lane, Newbury, Massachusetts, United States

Break out your lederhosen and join us on Saturday, October 21, from 12:00 pm-5:00 pm at Spencer-Peirce-Little Farm in Newbury, MA for Barktoberfest 2023!  We invite the entire Sweet Paws Rescue community to enjoy this fun-filled day of music, activities, and local food & drink in celebration of our southern team’s amazing efforts and dedication. […]

Cars for Charity Show

Cruiseport Gloucester 6 Rowe Square, Gloucester, United States

Cars for Charity show for several charities in the North Shore Boston region. Enjoy waterfront Gloucester and some exotic & classic cars!

Costume Crawl Boston 2023

West End Johnnie’s 138 Portland Street, Boston, Massachusetts, United States

The ONLY crawl with access to: West End Johnnies, Scholars, Hennessy's, Sissy K's, Hava, Wild Rover, Cask 'N Flagon & Six West Rooftop!

Salem Common Food Court 2023

Salem Common N Washington Square, Salem, Massachusetts, United States

Fiesta Shows hosts a food court on Salem Common. Hours vary based on weather and crowd conditions. 

2023 Taste of the Town: Eat and Drink Local at the CYC

Corinthian Yacht Cub 1 Nahant Street, Marblehead, Massachusetts, United States

The Marblehead Chamber of Commerce invites the public to join us for our “Taste of the Town – Eat Local, Drink Local” event on Friday, November 3, 2023 at the Corinthian Yacht Cub, located at 1 Nahant Street, Marblehead. All are welcome and encouraged to attend!  Tickets are $50 in advance and $60 at the […]

Pumpkintime Night Market

Artist's Row 24 New Derby Street, Salem, Massachusetts, United States

P U M P K I N T I M E is a haunted farmlands themed extravaganza on Artists' Row with all ages in mind. This fantasy night market and festival centers the odd and the unusual side of magical culture. Join us for an evening of interactive games, music, performance art with strange characters […]

Wicked Kidz Fun Races at GUS 2023

Glen Urquhart School 74 Hart Street, Beverly, Massachusetts, United States

We are excited to again partner with Wicked Running Club to bring back the Wicked Kidz 1/2 Mile and 1 Mile races. This is a free, professional-style race event with race bibs and awards, just for the kids. We had so much fun last year, and can’t wait to do it again this fall!

Boston’s Official Holiday Tree Arrival

Boston Common 139 Tremont Street, Boston, Massachusetts, United States

This is the 52nd year that a tree has been donated, and commemorates 105 years of friendship with Nova Scotia after the people of Boston provided emergency assistance when Halifax, Nova Scotia’s capital, was devastated by a maritime munitions explosion in the harbor in 1917. The first Tree for Boston was donated in 1971 by […]

Wild Turkey Trot

Winner's Circle 211 Elm Street, Salisbury, Massachusetts, United States

Cool weather fall running is back! This year the Winner's Circle Running Club has moved their annual 5K to Salisbury. Registration opens at 7:00 am and the race starts promptly at 8:30 am. They feature runner and family friendly trails, and post race refreshments. The new course which is primarily on a rail trail offers […]

Holiday Lights Fest

Good Pickin' Farm 5 Gould Road, Westford, Massachusetts, United States

Enjoy a fun-filled night with the family strolling through light and holiday displays, visiting with Santa, hayrides, live music, sweet treats and more!

Newburyport’s Santa Parade and Tree Lighting

Waterfront Park 36 Merrimac Street, Newburyport, Massachusetts, United States

For more than three decades, Newburyport has rung in the start of the holiday season by welcoming Santa and Mrs. Claus as they arrive by U.S. Coast Guard boat. Traditionally held on the Sunday after Thanksgiving, Santa’s arrival is followed by a parade through Newburyport that ends at Market Square, where Santa and community leaders […]

Marblehead Christmas Walk

Celebrate the 52nd Annual Marblehead Christmas Walk & Holiday Stroll! Well known as one of the finest holiday happenings in New England, Marblehead Christmas Walk is a signature event that captures the warmth of the holiday season throughout the entire town. This is a time when Marblehead’s historic charm shines bright, and the festive spirit […]

Frog Pond Skating Spectacular

Boston Common Frog Pond 38 Beacon Street, Boston, Massachusetts, United States

Join the City of Boston and The Skating Club of Boston for a free ice show featuring competitive figure skaters from The Skating Club of Boston. The outdoor shows offers the public a chance to see national and international competitive figure skaters, soloists, groups, wee skaters, and Team Excel Synchronized Skating and Theatre On Ice […]

Boston Common Tree Lighting Ceremony

Boston Common Visitor Center 139 Tremont Street, Boston, Massachusetts, United States

Join the official holiday season kick-off in Boston - the lighting of the City of Boston's official Christmas tree and trees throughout Boston Common and the Public Garden. Mayor Michelle Wu, the Boston Parks and Recreation Department, and title sponsor The Province of Nova Scotia will host Boston’s signature holiday celebration, the 82nd Annual Boston […]

Holiday Invitation Nights 2023

Downtown Newburyport Newburyport, Massachusetts, United States

Mark your calendars, book a babysitter, and call your friends to make plans for three great nights in Newburyport! Enjoy merchant hospitality, live entertainment, shopping, and dining in beautiful and festive downtown Newburyport, The Tannery, Merrimac Place, and Horton's Yard.  Spend your evening strolling from shop to shop as you stock up on holiday gifts while […]