Brewster Historical Society
Authors: Marco & Angelo

Authors: Marco & Angelo

We own the Candleberry Inn, a boutique bed and breakfast in central Cape Cod. We're glad to share our recommendations on all the great things to explore throughout Cape Cod.

Your Complete Guide to Brewster Historical Society Attractions, Events, & More

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    When it comes to planning a Cape Cod getaway, there’s no shortage of activities to put on your itinerary — beaches, boating, hiking, and art galleries to name a few. And, history buffs will fall in love with the Cape’s rich past.

    Offering a taste of that history, the Brewster Historical Society gives you some insight into what life was like in this quaint town. It maintains and manages two historic sites, as well as offers events throughout the peak season. Here’s everything you need to know before you plan your visit.

    For more historic sites and museums — like the Cape Cod Museum of Natural History or JFK Hyannis Museum — check out our free Cape Cod Vacation Guide. It also includes recommendations for recreational activities and restaurants across the Cape.

    Brewster Historical Society
    Brewster Historical Society | photo courtesy of gallery511

    Brewster Historical Society Attractions & Things to Do

    Founded in 1964, the Brewster Historical Society is a non-profit organization that collects and preserves historic Brewster-related artifacts, documents, photos, and more. Its two main attractions are the Cobb House Museum and Windmill Village.

    Both of these historic landmarks are open for tours and demonstrations on Saturdays during the peak season — mid-April through Indigenous Peoples Day. But, you’re always welcome to explore the gardens and grounds, which are ideal for photo ops.

    Cobb House Museum

    The Cobb House Museum is the Brewster Historical Society’s main building. The organization has restored and renovated the 1799 house since its purchase in 2015, turning it into the first sea captain’s home to be open to the general public as a museum.

    The renovation was made possible with donations from businesses and residents who wanted the landmark to remain alive, in addition to state grants.

    Except for the indoor plumbing, everything in the historic house is just as it was more than 200 years ago — including the beehive oven, fireplaces, flooring, and windows — preserving the legacies of two significant Brewster citizens — Captain Elijah Cobb and great-granddaughter Caro Dugan.

    Captain Cobb

    Born in 1768, Captain Cobb commanded the Jane, Monsoon, Paragon, and Ten Brothers ships throughout his life. Arguably the most famous sea captain in Brewster, he traveled the world. In the late 1700s, he purchased a farm and built the now historic home in 1799 to move in on New Year’s Day 1800.

    After sailing again and becoming a prisoner of war during the War of 1812, a prisoner exchange allowed Cobb to return to his home. Then in 1820, he retired from sailing and served several civic posts in Brewster until his passing in 1848.

    A record of Cobb’s life as a sea captain is published in the Yale University Press, and he’s listed on the National Register of Historic Places as the first person of historical interest in the Old King’s Highway Historic District — a designated area that stretches from Sandwich to Orleans.

    Caro Dugan

    Born in 1853, Caro Dugan (Cobb’s great-granddaughter) lived most of her life in the historic Cobb home with her mother, Helen. After her father died, her mother took in summer boarders to fill a financial gap.

    Professional photographer Cornelius Chenery started boarding here in 1888, and he and Dugan had a close relationship. The Brewster Historical Society has more than 400 glass plate negatives from the photos that the pair took of the Cobb house and town life. Also, the Brewster Ladies Library published Dugan’s lively, colorful diary — dated 1873-1878.

    The Cobb House remained in the family until Dugan’s passing in 1941 and eventually came under the ownership of the Brewster Historical Society.

    Museum Exhibits

    Visiting the Cobb House Museum takes you back in time. Each room has a themed exhibit — four permanent galleries and a special exhibition area. The exhibits include antique furniture, medicine bottles, paintings and portraits, old tools, and other Brewster-related artifacts that the Brewster Historical Society has collected over the years.

    Additionally, there’s an extensive photograph and document research area, which you can access with an appointment. The organization has recently completed creating a vintage Woodworking Shop in the Cobb Annex too. And each year, the organization holds Open House events for free museum admission.

    Windmill Village

    Next to Drummer Boy Park, Windmill Village consists of three historic structures managed by the Brewster Historical Society — Higgins Farm Windmill, Harris-Black House, and Hopkins Blacksmith Shop. The public is welcome to tour the village and watch blacksmithing demonstrations on weekends during peak season.

    Higgins Farm Windmill

    The windmill was originally built in 1795 near what is now the corner of Ellis Landing Road and Route 6A — about 5 miles east of its current spot. The structure is so special because of its elaborate design and detail — some of which resemble a ship.

    It’s believed that the structure was moved about 100 yards down Ellis Landing (unknown time) because the creaking arms were scaring passing horses. Before coming to its current location, it was moved again around 1890 to the Roland Nickerson estate (now Ocean Edge Resort) as a private golf course clubhouse.

    Harris-Black House

    This home is one of the oldest early American houses to be built on Cape Cod and is often referred to as an original “small house.” It’s believed that it’s the only small early house still standing on the Cape.

    The 16-foot square house was built in 1795 and was home to a family of eight. As it was passed down through the family, it has been a cranberry storeroom and a small forge. Eventually moved to its current spot, the house was restored by John MacKenzie.

    Hopkins Blacksmith Shop

    Henry Hopkins and his father, Moses, built this blacksmith shop in 1867 on Depot Road. He made hinges, hooks, pulleys, and other tools, as well as shod horses. The wood forge is its most unusual feature because most restored forges are brick or stone — wood forges seldom survive time.

    The Brewster Historical Society purchased the shop in 2009 and moved it to Windmill Village before restoring it to nearly authentic condition.

    Biking Between Landmarks

    If you enjoy biking, you can cycle to Cobb House Museum, storing your bike on the rack at the end of the parking area. Then, you can cycle nearly 2 miles west to Windmill Village via Lower Road.

    A pretty straight shot, the route on Lower Road doesn’t have a lot of traffic. Along the way, you’ll come across the Eddy Sisters Trail on the left at the Community Garden. Not too much farther down the road, the Eddy Bay Trail will be on the right — it ends at the town’s highest bluff overlooking Cape Cod Bay.

    After about 1.5 miles, Lower Road ends and merges into Route 6A (aka Main Street or Old King’s Highway). You’ll cycle about another half-mile before turning left onto Drummer Boy Road, reaching Windmill Village, which also has bike racks.

    Cobb House, Brewster Historical Society
    Cobb House, Brewster Historical Society | photo courtesy of visithousemuseums

    Events With the Brewster Historical Society

    The Brewster Historical Society hosts a variety of events at the Cobb House Museum and Windmill Village throughout the peak season. Some of these events include miniature tours of Brewster Massachusetts and book and history discussions with authors.

    In 2022 and 2023, for instance, the organization hosted the Haunts and Habitats Walking Tour — a 1-hour guided tour of historic Route 6A, featuring details about antique homes, influential citizens, brave sea captains, and more.

    In 2023, the Brewster Historical Society hosted The Revolutionary War Experience at Windmill Village — an event in which members of the Brewster Colonial Artillery Company and Yarmouth Minutemen dress in period attire to demonstrate manual arms, as well as offer other activities.

    Unique events aren’t all that the organization coordinates, though. It offers annual festivities too!

    Brewster in Bloom Festivities

    Every late April and early May, the town shows its colors during the Brewster in Bloom festival. The Brewster Historical Society joins the foray by offering festivities at the Cobb House Museum and Windmill Village.

    Annual Drummer Boy Open-Air Antiques Fair

    In June of every year, Windmill Village and Drummer Boy Park come alive for the Antiques Fair. You’ll find antique and vintage items from more than 40 exhibitors.

    TIP: You can get discounted entry to the fair with a coupon on the Brewster Historical Society’s website.

    On top of that, there will be an Antique & Classic Car Show on-site, as well as access to everything at Windmill Village.

    Brewster for the Holidays Festivities

    When the town lights up for Brewster for the Holidays from late November, the Brewster Historical Society joins the celebration in a big way.

    It features a Victorian Holiday at the Cobb House Museum with period decorations and docents sharing period holiday stories. At Windmill Village, the historical society organizes special holiday-themed tours, refreshments, and singing in addition to lighting the windmill with hundreds of white lights.

    Places to Eat Near the Cobb House Museum & Windmill Village

    You could spend several hours exploring all that the Brewster Historical Society has to offer, so you’re bound to get hungry at some point. Fortunately, the Cobb House Museum and Windmill Village are only a short bike or car ride from some of the best Brewster restaurants.

    Kate’s Seafood

    Just a 2-minute drive or a 5-minute bike ride east of Windmill Village, Kate’s Seafood is ideal if you’re in the mood for a quick bite of seafood. This seasonal walk-up restaurant serves some of the best fried fish and shellfish in the area. The menu includes lobster and crab rolls, hot dogs and burgers, grilled seafood, and ice cream as well.

    Cafe Alfresco

    A little farther down Route 6A within Lemon Tree Village, Cafe Alfresco is a fantastic spot for lunch. It serves some of the best sandwiches in the Lower Cape, and even Cape Cod Life thinks so. You can order from a wide array of specialty sandwiches and panini, bowls, salads, and smoothies.

    The Brewster Store & The Brewster Scoop

    Only a 1-minute drive or 3-minute bike ride east of the Cobb House Museum, The Brewster Store is a fun place to get souvenirs, as well as various foods and candies — cranberry bog frogs, fudge, saltwater taffy, penny candy, and more.

    Right next door, The Brewster Scoop is a local favorite stop for ice cream. Open from Memorial Day through Labor Day, this shop has more than 30 flavors to choose from in addition to sugar-free and frozen yogurt flavors, as well as sherbet and sorbets. There are tons of toppings too!


    Just another minute down Route 6A, Spinnaker is a chic, Mediterranean boutique restaurant that specializes in creative seafood plates. The dinner menu is always changing based on the freshest, seasonal ingredients available. And, you can pair your dish with a glass of wine from an extensive list.

    The Brewster Fish House

    A little bit farther down Route 6a, The Brewster Fish House is a contemporary bistro that’s known for making classic New England seafood dishes with a sophisticated twist. Highly rated by Zagat, the restaurant offers intimate al fresco lunches and dinners with craft beer, unique cocktails, and eclectic wines.

    Exterior of Candleberry at Twilight

    Stay in a Historic Sea Captain’s Home at Candleberry Inn

    With Brewster known as The Sea Captains’ Town of Cape Cod for the 50-plus sea captains who have called it home, there are several other historic houses to see. At Candleberry Inn, you have the opportunity to stay in a former sea captain’s home. Best of all, the Cobb House Museum is only a 5-minute walk away — or faster if you bike.

    Our circa 1780s–1790s Georgian-style inn is the perfect place to live in historic quarters while you’re visiting Cape Cod. We have guest rooms and suites in the main house and our carriage house, giving you a variety of distinct lodging options to choose from. We even offer special packages to enhance your stay.

    When you’re ready to book accommodations for your Cape Cod getaway, check our availability!

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