Local Events & Festivals

Holiday Fun On Cape Ann Enjoy the traditions of this picturesque town and embrace the Holiday Spirit with local events centered around celebrating the most wonderful time of the year. Search our wide selection of vacation rentals scattered down the rugged enchanting coast of Cape Ann and find the perfect beach house to host your  […]

Enjoy A Trip This Fall To Cape Ann As summer fades and the leaves begin to change, Cape Ann, Massachusetts, transforms into a stunning autumn wonderland. This picturesque region offers the perfect backdrop for a fall getaway, whether you’re planning a quick trip from Boston, a weekend escape, or a peaceful mid-week stay. We’re highlighting […]

Even though the holiday season can get expensive after the gifts, decorations and other related items are purchased, the good news is that the “holiday spirit” is free! There are plenty of free events and activities on Cape Ann and across the North Shore to put you in a festive mood. Here are some of our […]

Celebrate the Gloucester 400+ anniversary in 2023 in Gloucester, MA!

As you start planning your fall Cape Ann getaway, check out these fantastic events and festivals coming up in September and take advantage of our lower-off season vacation rental rates.

Getting outdoors and out to the farms for apple picking, pumpkin picking, and getting lost in corn mazes are some of the most popular fall kid activities we’ve found. There are also many family-friendly festivals and events to choose from that celebrate autumn’s bounty and also every kid’s favorite spooky holiday, Halloween. Below are some of our […]

Fall is a great time to take a weekend getaway with family or friends. While the weather may be cooling off, there’s still a cornucopia of seasonal activities to do while visiting Cape Ann. Staying in one of our vacation rental homes will keep you close by where the activities happen to be. We love Cape […]

Spring activities and events on Cape Ann include whale watching, festivals, concerts, art exhibitions, and more. Plan your visit now!

Whether you are a maritime expert, a history buff, an art lover, or a Halloween enthusiast, you’ll want to add historic Salem to your travel list. Known as the “Witch City”, Salem is a fantastic place to visit year round, though October is the month to experience Halloween at its best. Your Beverly or Cape […]

The Gloucester Schooner Festival is THE maritime event of the year in Gloucester! This 3-day festival over Labor Day Weekend brings sailors, spectacular schooners, and enthusiastic spectators from all over the world. The Schooner Festival celebrates Gloucester’s maritime history and honored status as America’s Oldest Seaport. All eyes will be on Gloucester’s beautiful harbor, which […]