All Ages

Trails & Sails

Explore the North Shore with over 150 Free Events in Essex National Heritage Area's Trails & Sails celebration in Massachusetts.

Essex National Heritage Area sites will offer over 150 free family fun events from September 14-29, 2024 for the annual celebration of TRAILS & SAILS. Discover special places in your backyard and be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds. Find what makes Essex County like nowhere else during Trails & Sails! It’s all FREE and it’s all located within the 34 cities and towns of Essex County.

When: 
Daily, September 13-28, 2025

Haunted Biz Baz Street Fair

The Biz Baz Street Fair in Salem Massachusetts hosts dozens of Chamber members and unique vendors selling handmade art, crafts, gifts, apparel, and more.

Come visit the Biz Baz Street Fair to see over 80 vendors and enjoy the historic Salem Common. Vendor sales include handmade jewelry, art, apparel, crafts, Halloween decor and so much more! The Biz Baz will be in the Salem Common and you can shop on Saturday, October 4, from 10AM-6PM, and Sunday, October 5, from 10AM-6PM. This event brings thousands of visitors, so you do not want to miss out! Hosted by the Salem Chamber of Commerce.

When: 
Saturday, October 5, 2024 10am-6pm
Sunday, October 6, 2024 10am-6pm
Location: 

Jan's Pitch for Breast Cancer and the Arts

Come to a vintage baseball match that raises funds for breast cancer research at Spencer Peirce Little Farm in Newbury

Join Spencer-Peirce-Little Farm and the Essex Base Ball Association for a day of vintage base ball as we celebrate the 20th season of this partnership! The four teams of Essex Base Ball, the Newburyport Clamdiggers, Lowell Base Ball Club, Portsmouth Rockingham's, and the Lynn Live Oaks, play using 1864 rules. At these fun, historically accurate games, gloves are not allowed, players pitch underhand, and a ball bounced once and caught is an out. Bring a picnic or partake in beer and hot dogs from our friends at Ipswich Ale!

When: 
Sunday, October 5, 2025 11am-3pm

Newburyport Chocolate Tour

The Newburyport Chocolate Tour is a chance for chocolate lover to experience the best treats of Newburyport Massachusetts!

A sweet stroll with a purpose— The Chocolate Tour is a community-driven tasting experience through the charming streets of downtown Amesbury and Newburyport. Local shops serve up chocolate delights while you explore, shop, and support amazing causes.
Even sweeter? Every ticket helps fund local nonprofits—so while you indulge, you're also giving back to the community.

When: 
Saturday, October 4, 2025 5-7pm

Walk Against Domestic Violence

Jeanne Geiger Annual Walk Against Domestic Violence in Newburyport Massachusetts

The Walk Against Domestic Violence is hosted by Jeanne Geiger Crisis Center in Newburyport, Massachusetts. We walk because it could be your best friend, your younger sister, the man who works in the office next to you, your child's best friend, or the teenage girl who works in the local coffee shop. We walk because domestic violence doesn't have a face, because it could happen to anyone, at any time. Walk with us as we advocate for change and raise awareness for domestic violence.

When: 
Sunday, October 5, 2025 9-12pm

GNOCA 5K Run/Walk

GNOCA's 5K Run/Walk in Honor of Jackie Poor & Paula Holm is a 5k Run or Family Friendly Stroll through Scenic Newburyport starting & ending at Michael's Harborside. Tee Shirts will be given to the First 100 Registrants. All participating runners will be assigned numbers and timed. Great Prizes for Age Category Winners!

When: 
Sunday, September 28, 2025 8AM-1PM

Paddle Around Historic Rockport Harbor

Paddle around Rockport Massachusetts Harbor for FREE as part of Trails and Sails

Come join North Shore Adventures and Outdoor Center for some fun on the water! No experience necessary. Depart from our private beach in one of our safe, stable kayaks or paddle boards and paddle around the historic Rockport Harbor for 30 mins. See lobster boats, Motif #1, the Rockport Break water, and the gorgeous Head Lands property. This is your only chance to kayak/SUP for free!! Come join us any day Sept. 13-28 at 10:30am.

When: 
Daily, September 13-28, 2025 10:30-11am

Climb Up Gloucester City Hall Tower

Take a Free tour of Gloucester Massachusetts City Hall's renovated tower as part of Trails and Sails 2024!

Experience the WOW factor when you climb up Gloucester’s City Hall clock and bell tower and emerge at the bell level. Views, weather permitting, are awesome. Members of Gloucester’s City Hall Restoration Commission will be on hand to inform you of the history of this architecturally significant building that had graced Gloucester’s skyline for more than 150 years. Please note that while the tower is not handicapped accessible the WPA Murals in City Hall are accessible and are one, if not, the best collection of WPA murals in the Commonwealth.

When: 
Saturday, September 27, 2025 Noon-3pm

Choate Island Day

Choate Island Day with the Trustees of Reservations in Ipswich Massachusetts

Spend a day with the Trustees of Reservations in celebration of Choate Island – the crown jewel of the Crane Wildlife Refuge. Here deer and foxes roam through fields that once housed herds of sheep, and osprey fly over breathtaking views of Essex Bay. The island was first home to indigenous farmers and fishers, then to generations of the Choate family, and was later a retreat for Cornelius and Miné Crane, who loved the place so much they decided to be buried at the summit.

When: 
Saturday, September 27, 2025 10AM-3PM
Last Admission at 1pm

Maritime Adventure Days

Maritime Adventure Free Days at Custom House Maritime Museum Newburyport Massachusetts

Maritime Adventure Free Days offers families and kids a unique opportunity to explore maritime history through interactive activities, guided tours, and hands-on workshops. A day of fun and discovery at the Custom House Maritime Museum for the family. These free Saturday events include experiencing a traditional Wampanoag dugout canoe being made by a team of craftsmen. Part of Trails & Sails

When: 
Saturday, September 13, 2025 9am-1pm
Saturday, September 20, 2025 9am-1pm
Saturday, September 27, 2025 9am-1pm

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Landmark Summer Program at Landmark School in Beverly Massachusetts

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Nice n' Easy Hike at Breakheart Reservation

Nice and Easy winter hike at Breakheart Reservation in Saugus Massachusetts
Join the Park Interpreter for this weekly guided hike! Each trip will highlight natural and historic features unique to Breakheart. Hikes are moderately paced and range from 2-3 miles over sometimes uneven and rocky terrain. Best for ages 8 years and up. Meet at the Visitor Center.
9:30 am to 11:30 am

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 pm

Gloucester's So Salty 2026

Celebrate Gloucester Massachusetts recognizably salty character with local cultural institutions in the heart of downtown.
Celebrate the fish city’s recognizably salty character with local cultural institutions and businesses during the 5th Annual Gloucester’s So Salty festival sponsored by the Cape Ann Museum in partnership with Discover Gloucester! This annual event brings over 2,000 people to the downtown area each...
10:00 am to 4:00 pm

Native Seed Sowing at Long Hill

Seed Sowing Workshop at The Trustess of Reservations' Long Hill Gardens in Beverly Massachusetts
Join Cole Campbell, production horticulturist at Native Plant Trust, for this native seed-sowing workshop at Long Hill Public Garden in Beverly, MA. Learn about our native plant seeds, and then get your hands in the soil to sow some seeds that you can take home with you.
11:00 am to 12:30 pm

Saturday, February 14

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Discover Saturdays at Cape Ann Museum

Discover Saturdays for Families at Cape Ann Museum in Gloucester Massachusetts
Enjoy a FREE guided activity (ages 4+) in the gallery. Learn about Cape Ann’s Granite Industry, try a fun art making activity, and join in gallery tour designed for kids and their caregivers, led by a CAM Educator. Afterwards grab a scavenger hunt to explore the property and enjoy the lawn.
10:00 am to 12:00 pm

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 pm

Quarry Quest Treasure Hunt

Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
10:00 am to 2:00 pm

StoryWalk at Halibut Point

StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
10:00 am to 2:00 pm

February Vacation at MIT Museum

Kids will have a blast at the MIT Museum in Cambridge Massachusetts during February Vacation Week!
Come on your own, with friends, or bring the whole family to the museum for a special week of programming. The museum has a number of activities planned for the week of February 14-22, including extended Maker Hub and Learning Lab hours, tours, gallery cart demos and family workshops. With the...
Where: MIT Museum
10:00 am to 5:00 pm

Sunday, February 15

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Wonderful Winter Birding

Beginning winter birding is held on the 3rd Sunday of each Winter month at Halibut Point State Park in Rockport Massachusetts
Halibut Point State Park, along the Atlantic migratory path, is an excellent locale for winter birding species you rarely see anywhere else.Winter brings birds and ducks from frozen ponds up north to our seashore. See Harlequin ducks and loons among the winter visitors at this rocky coastal water’s...
8:00 am to 10:00 am

Quarry Quest Treasure Hunt

Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
10:00 am to 2:00 pm

StoryWalk at Halibut Point

StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
10:00 am to 2:00 pm
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