Instead of Kennebunkport, This Massachusetts Town is Where You Should Take Your Next Trip

I’ve been vacationing in Kennebunkport, Maine, and the surrounding towns since high school. And I especially appreciate traveling through an area steeped in history, charm, and a bit of intrigue, which is why I love it so much. However, a recent trip to Brewster, Massachusetts, immersed me in a beautiful history lesson that allowed me to experience several days in a Gilded Age Mansion, learn all about a town established by a Mayflower passenger (William Brewster), and experience the beauty of a historic seaside town.

Why This Town Feels Like Kennebunkport

Similar to Kennebunkport, Maine, which has a rich sea captain history, Brewster, Massachusetts, is a Massachusetts town like Kennebunkport that has a very colorful history that’s rich in sea captain lore and beautifully archives life by the sea from times past. Both Kennebunkport and Brewster have seasonal summer vacationers, quaint shopping areas, and lots of maritime history. Both have lots of options for boating and leisurely activities. Yet, Brewster is truly a hidden gem in Massachusetts, and it is the perfect dupe for the overcrowding of streets, restaurants, and beaches that readily occurs throughout the summer months in Kennebunkport. Yes, summer is a busy season for sure in this cozy Cape Cod town, but there’s a relaxation and restorative essence that this quaint town carries that truly sets it apart from Kennebunkport, and altogether, Brewster is an underrated small town in Massachusetts, and still a bit slower, in a good way!

Though separated by state lines, Brewster, Massachusetts, and Kennebunkport, Maine, share a distinctly New England spirit shaped by the sea, history, and tradition. Both communities are nestled along rugged Atlantic shorelines where salt marshes, sandy beaches, and weathered harbors create landscapes of remarkable natural beauty. Their histories are deeply intertwined with maritime heritage, from fishing and shipbuilding to generations of sailors and merchants who helped define coastal life in the Northeast. Historic homes and village centers evoke a timeless charm, while local festivals, fresh seafood, and a strong sense of community celebrate traditions passed down through centuries. In both towns, visitors and residents alike experience a culture that honors its colonial roots, values its connection to the ocean, and embraces the relaxed rhythm of life along New England’s storied coast.

In Brewster, there are many accommodations for families with kids and teens, ranging from beachside villas to seasonal rentals and beyond. But staying at the historic Nickerson Mansion was the perfect fit for me. I love learning about history, experiencing spaces that offer some form of restorative rest and healing (I’m the mom of a teen and a toddler, so atmospheres conducive to rest win me over every time!), and being in places with a bit of charm.

Staying at this property on the Nickerson estate was unique and very interesting. The vintage chandeliers, ornate textiles and prints on plush fabric, and feminine curtains draped around cozy beds were everything I needed and more. It was truly a book lover’s delight with many dimly lit reading spaces, and eating daily in the Roscommon Room felt like stepping into another place and time. Not to mention, the property offers a Self Love Summer Wellness Program that is perfect for moms on the go who need to unwind. I took a sound bath, and I have to admit that it was quite illuminating, and I slept like a baby afterward!

Being on this property was elegant and hushed, yet there was an air of mystery coupled with the estate's otherworldly essence, and I relished it all. And, right next door, there’s a Carriage House that was established in 1890! It's so unique and interesting to literally walk through buildings and see remnants from the past. But for families traveling with lots of kids or family members, I’d recommend staying at the Endicott and Edinborough Villas (for the space!), and for romantics and those wanting “adult-only” vibes, I’d personally recommend The Charm (no kids allowed).

Why It’s an Even Better Choice

Initially, Brewster feels similar to Kennebunkport, but there’s an ease and an insulated quality about this cozy town that elevates the experience for those who want the essence of being by the water, but without the pretension of being a vacation or “summer town”. From the vintage signage, neatly manicured homes, decorative mailboxes, a well-preserved bookstore, a general store, and cute little coffee shops like The Peacemaker, this town has those precious “untouched details” that make it super special. And local businesses and properties like the Nickerson Mansion welcome community members and guests to partake in the town's wonderful uniqueness. I was pleased to learn that there are spaces at places like the La Salette Reading Parlor (Yes, the La Salette missionaries once occupied this property as well!) at the Nickerson Mansion that are open to people in town. 

Similar to the family-friendly swimming at Kennebunkport’s Gooch’s and Mother’s beaches, Brewster has many public beaches (Crosby Landing Beach and Saint's Landing Beach are my favorites) and private beaches like Bay Pines Beach that are wonderful for families with younger kids. The Brewster Flats on Cape Cod Bay stretch for miles, and kids will thoroughly enjoy being able to walk so far out on the beach. I especially loved walking through the clear water, looking at sea creatures as I headed to a Cape Cod Oyster Bed tour, where I learned all about the life of oysters!

What You Can Do Here

While Brewster is small enough to possibly enjoy in a day trip, there are so many delightful things to do over the course of a week, or even a full summer month. I believe that the world is one’s classroom, and with each place I visit, I’m always pleasantly surprised by how history is actually quite present. And like Kennebunkport, which houses many historic lighthouses and homes, Brewster offers many insightful museum tours, historic sites, and homes that are well-preserved and fascinating to experience. Lectures like “History Uncorked” at the Nickerson Mansion, and cultural immersion at places like the Cape Cod Museum of Natural History (you can take a beekeeping course!), Brewster Historical Society (the former home of real-life Sea Captain Elijah Cobb), the Stony Brook Gristmill and Museum, The Crosby Mansion (Think Queen Charlotte and Bridgerton, but “New England” style. Such a gorgeous space!), all make room for learning, in addition to athleaisure activities. 

Places like Boat Cape and Hyannis Whale Watcher Cruises make experiences on the water easily accessible. There are many opportunities for boating, playing pickleball, and indulging in self-care. The Beach House Spa in Brewster offers everything from deep-tissue facials and full-body massages to a “digital-free” zone and space for manicures and pedicures. And for those who prefer to bike or rollerblade, this Cape Cod town has cute places to shop, like Pelo Mar (if you have a teenage daughter who likes the “Coastal Granddaughter” aesthetic), which is a dream. My daughter absolutely loved their tanks, halters, and sundresses. And, if thrifting and vintage shopping are your thing, there are several places on and off Main Street to thrift.

Plan Your Visit and Conclusion

Anytime during the summer season, June through August, is a great time to visit Cape Cod towns similar to Brewster. If you want to beat the crowds, I’d say early June or even late August. If you visit during the spring, the town may be moving a bit more slowly, but if you want to be in the midst of it all, I’d definitely lock in a trip for July or early August.

If you’re traveling with a family and plan to do water sports, swimming, and beach play, make sure to research how close or far away your hotel or vacation rental accommodations are to the water. (There’s nothing like being able to walk right out to the beach when you have a toddler, or multiple kids in tow.) And if you travel often with kids who are many years apart, research the activities you want to do ahead of time and discuss sleeping arrangements. Most teens love having their own suite so they can sleep in! Also, dog owners need to know that Brewster prohibits dogs from public beaches, the Brewster Flats, and ponds from May 1st to October 1st each year.

If you want to keep your next New England vacation cozy, cultured, and quirky in a beachy way, Brewster is a wonderful place to plan for an extended stay.