North of Boston

Peach & Sunflower Festival
2025-08-10 10:00 - 18:00, 2025-08-16 10:00 - 18:00, 2025-08-17 10:00 - 18:00 (America/New_York) | Cider Hill Farm, 45 Fern Avenue, Amesbury, M, 01913, United States
Cider Hill Farm is celebrating all things sunshine, flowers and peaches! The multi-weekend event features cut-your-own farmhouse bouquets, free live music, hard cider bar, tastings, activities, hayrides, food trucks, peach treats, and pick-your-own peaches. RSVP now to get it on your calendar and then purchase pick-your-own peach tickets and cut-your-own flower tickets later or when you arrive!

Country Fair at Cider Hill Farm
2025-08-30 08:00 - 2025-09-01 18:00 | Cider Hill Farm, 45 Fern Avenue, Amesbury, M, 01913, United States
Visit Cider Hill Farm on Labor Day weekend for a quintessential New England celebration welcoming the season’s bountiful harvest! Enjoy summer apple picking, free tastings, hard cider, classic fair foods, fall flower cutting, old time-y games, free live music, tractor rides & more! See event schedule as we add more happenings to the line-up! Free admission (does not include pick-your-own tickets, food or drinks).

Gloucester Harbor - The Soul of Cape Ann
2025-09-05 - 2025-09-07
“Gloucester Harbor – The Soul of Cape Ann” is the focus for a weekend of multidisciplinary talks, readings, and tours exploring Gloucester’s amazing natural harbor and its impact on Cape Ann’s history, commerce, and the arts. Organized by the Jonathan Bayliss Society in partnership with Cape Ann Museum, Gloucester Marine Genomics Institute, Gloucester Writers Center, Maritime Gloucester, Mass Oyster Project, Neptune’s Harvest, Sawyer Free Library, and Schooner Adventure. Advance registration required via jonathanbayliss.org/harbor. Multiple locations in Gloucester, Mass.

Trails & Sails
2025-09-13 - 2025-09-28 | Essex County, Massachusetts
Now in its 24th year, Trails & Sails is your ticket to adventure across Essex County, Massachusetts – a region recognized as a National Heritage Area for its rich history, cultural treasures, and natural landscapes. Each September, this vibrant event series provides access to hundreds of unique experiences such as guided hikes and paddles to behind-the-scenes tours, historic reenactments, interactive exhibits, artisan demos, community celebrations, and much more. Whether you’re a history buff, nature lover, or just curious to discover something new to love in your own backyard, Trails & Sails has something for everyone.

Flying Aces Take Flight!
2025-09-13 11:00 - 14:00 | Spencer Peirce Little Farm, 5 Littles Lane, Newbury, M, 01951, United States
Join the Flying Aces and Spencer-Peirce-Little Farm for a day of family fun and flying! The Flying Aces Club will race free-flight stick-and-tissue model airplanes. Attendees will have the chance to make models take flight and learn about the history of the Plum Island Airport, one of New England’s oldest airfields. Admission includes a model airplane and raffle tickets. Pack a picnic, visit with the animals, and enjoy face painting and airplane art-making. Great for all ages!

Fall Fest Beverly
2025-09-13 17:30 - 21:30 | Odell Park, Rantoul Street, Beverly, Ma, 56-98 Broadway, Beverly, M, 01915, United States
Beverly Main Streets will be hosting their annual Fall Fest (formerly the End of Summer Party) on Saturday, September 13 from 5:30-9:30pm (with a rain date of 9/14/25). Visit Odell Veterans Memorial Park for live music and entertainment, food vendors, and a variety of activities hosted by local businesses and organizations. From there, walk Rantoul St and Park St for shopping and dining at downtown businesses.

Sixth Annual Fall Fair
2025-10-04 10:00 - 15:00 | Jeremiah Lee Mansion Gardens, 161 Washington St, Marblehead, 01945, United States
Join Discover Marblehead and the Marblehead Museum for the 6th Annual Fall Fair on Saturday, October 4th from 10:00am – 3:00pm. It’s sure to be a fun day in the Lee Mansion Gardens with Bubble Bar Boston serving up awesome drinks, music by Paul Simonelli, Intuitive Card Readings with Creative Spirit, Rule of Thirds Photo Booth, Acorn Gallery Students drawing portraits, and an amazing line-up of artist vendors selling their beautiful work.
As always, we will be selling Pumpkin Decorating Kits and donating all the proceeds to Marblehead Food Pantry. This event is rain or shine. Free admission. Come out and get an early start on your holiday shopping. Location: 161 Washington Street, Marblehead, MA.

Barktoberfest (Sweet Paws Rescue's 10th Annual Fundraiser)
2025-10-18 12:00 - 17:00 | Spencer-Peirce-Little Farm, 5 Littles Lane, Newbury, M, 01951, United States
Join Sweet Paws Rescue (a local nonprofit) for Barktoberfest 2025 – our 10th annual celebration of rescue, community, and the incredible dogs and people who make it all possible!
What’s Happening:
🐾 Live music and local food & drink vendors
🐾 Free kid-friendly games, crafts, and activities for the whole family
🐾 Free dog-friendly activities, dog park, and pet-friendly vendors
🐾 Meet adoptable pets and connect with some of our southern rescuers
🎟 Tickets: $12 per person | $40 per family | Kids under 10 FREE

Downtown Trick-or-Treat
2025-10-23 16:00 - 18:00 | Cabot St, Cabot St, Beverly, MA, 01915, United States
Downtown Trick-or-Treat is a free community event brought to you by Beverly Main Streets and the City of Beverly. Bring your costumed little ones down to Cabot St for free treats! Look for the orange flyer in windows of participating local businesses.

A Vintage Hallowe'en: Hawthorne Hotel's Annual Costume Ball
2025-10-25 19:30 - 23:55 | Hawthorne Hotel, 18 Washington Sq. West, Salem, 01970, United States
The event, introduced in 1990 and hosted by the Hawthorne team, features a live band (American Midnight), two DJs, interactive experiences, a costume contest, stationed hors d’oeuvres, and cash bars across three floors. Dance, people-watch, take selfies in front of our photo backdrops and enjoy being part of the premier bucket-list Halloween event in New England. Celebrate A Vintage Hallowe’en and pay homage to the hotel’s 100th anniversary with an unforgettable evening of eerie elegance and vintage oddity.

Self-Guided Fall Orchard Walk at Cider Hill Farm
2025-11-01 08:00 - 14:00, 2025-11-02 08:00 - 14:00, 2025-11-08 08:00 - 14:00, 2025-11-09 08:00 - 14:00, 2025-11-15 08:00 - 14:00, 2025-11-16 08:00 - 14:00, 2025-11-22 08:00 - 14:00, 2025-11-23 08:00 - 14:00 and 2 more dates | Cider Hill Farm, 45 Fern Avenue, Amesbury, M, 01913, United States
Bundle up and get out amongst the farm’s 10,000 fruit trees. Enjoy the fresh air and views as you walk through the orchards. Open Saturdays and Sundays 8 a.m. – 2 p.m from Saturday 11/1 – Sunday 11/30. FREE. No registration required. Closed weekdays and weekend afternoons. We want you to have a beautiful space to come and be! Area closures possible.
The farm store is open daily 8 am – 6 pm through December 14.

North Shore Food & Gift Emporium
2025-11-20 16:00 - 20:00 | Willowdale Estate, 24 Asbury Street, Topsfield, M, 01983, United States
NorthShoreEmporium.com
Located at Willowdale Estate • Topsfield, MA
Thursday • November 20, 2025
4 — 8 PM • $8 Admission
The tradition continues! Instead of a holiday craft fair, think of us as a holiday cocktail party surrounded by a festive marketplace filled with local artisans and merchants. All nestled within a gorgeous historic mansion, it’s the most delicious and decadent event of the season.
Returning to our roots, we’re thrilled to be where the magic first began… at the charming Willowdale Estate. Situated indoors throughout the estate, we’ve designed a luxurious shopping experience that’s both intimate and spacious. Plus a cash bar with savory snacks to enjoy.
This event is a celebration of local food + gifts. Who knew there were so many talented entrepreneurs in our midst? We’ve curated the most amazing selection of talented makers and merchants for an unforgettable evening of tasting + shopping.
Admission is $8, with a portion of the proceeds to be donated to our non-profit partner, Beverly Bootstraps.
Created + organized by two friends who share a deep love for the North Shore and all things local:
Lauren Guley
&
Jessica Brand
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★ BONUS ★
All guests will receive an Emporium tote bag. Seriously, who couldn’t use another canvas bag? Big, beautiful, and strong . . . perfect for placing all your goodies into as you shop the Emporium.
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Due to the limited amount of tickets, we encourage you to reserve yours as soon as possible. See you soon!

Theatermakers Of Today: First Annual Fringe Festival
2025-11-22 13:00 - 19:00 | Gloucester Stage, 267 East Main St., Gloucester, MA, 01930, United States
We are Theatermakers Of Today, and we are collaborating with Gloucester Stage to put up the TOT First Annual Fringe Festival!
Come and see a collection of incredible pieces of art in all different stages of the creative process. We have invited aspiring playwrights, performers, actors, directors, and all other types of theater-makers to submit and perform their work at the festival for you all to see! This festival serves as a platform where artists can confidently experiment with their in-progress work in front of a real audience. Bring your friends and family for a full day of theater!
You can also plan to have a few drinks, have more than a few laughs as our talented Emcee keeps you entertained between pieces, and at the end of the night vote on the 3 top performances to win 3 cash prizes! We cannot wait to see you there!

New England Equine Rescue's The Mane Event Dinner and Auction
2025-11-22 18:00 - 22:00 | Ipswich Country Club, 148 Country Club Way, Ipswich, M, 01938, United States
The Mane Event dinner and auction, New England Equine Rescue’s largest fundraising event each year, is scheduled for November 22, 2025 at the beautiful Ipswich Country Club in Ipswich, MA. The evening will feature good friends, a lot of fun, and a delicious dinner while raising money for NEER’s rescue efforts through silent and live auctions, a wine pull, and ticketed drawings. For event tickets and a preview of the auction items, please visit our event page.

Annual Beverly Holiday Parade
2025-11-30 13:00 - 15:00
A Beverly tradition since 1947, it includes floats, music, candy and Santa. Check it out!

Makers Market presented by Pentucket Arts Foundation
2025-12-06 09:30 - 15:00 | Veasey Park, 201 Washington St, Groveland, MA, 01834, United States
Join us at Veasey Memorial Park for the 6th Annual MAKERS MARKET, Pentucket Arts Foundation’s very own all-local, handmade holiday arts, crafts, and vintage clothing fair! You won’t want to miss the 38+ vendors, small business owners, and artisans in a charming holiday location. New this year: Wreaths & greenery by the Groveland Garden Club! Featuring live music performed by local students and homemade food in our cafe! Shop local and support the arts this holiday season!

Holiday Wreath Making Class
2025-12-11 19:00 - 21:00 | Beauport Hotel Gloucester, 55 Commercial Street, Gloucester, MA, 01930, United States
Create your own festive wreath at Beauport Hotel’s annual Wreath-Making Workshop with Meredith McCarthy on Thursday, December 11th from 7:00PM-9:00PM. Enjoy lush winter greenery, a custom bow, ocean views, and a cash bar while you craft. Tickets are $85 and non-refundable—space is limited, so reserve your spot today!

Downtown Winter Market
2025-12-12 16:00 - 20:00, 2025-12-13 08:00 - 17:00 | Beverly, 191 Cabos str, Beverly, United States
On December 12 and 13, Beverly Main Streets will host its annual Downtown Winter Market, designed to promote shopping small and activating spaces for the holiday season. Local businesses will be open for shopping and special activities from 4 to 8 pm, and vendor markets can be found at key venues. Find musical performances and special guests throughout both nights as you meander through our two main downtown streets. The Winter Market will focus on Cabot Street on December 12 and Rantoul Street on December 13.
