A Cape Cod vacation is a dream shared by people from all over the world, and if you are about to make your own dreams come true with a visit to our sandy shores, you may be wondering which town or village you should choose for your destination. Cape Cod isn’t all that large, but each of the towns and villages that make up its landscape offer distinctly different vibes and personalities, so we at Pretty Picky Properties thought we would shine a spotlight on the communities, giving visitors a peek into the activities, attractions, even the restaurants that shine brightest, helping make the decision a little easier. This Brewster guide is where we are starting and as you explore the town, we would like to invite you to explore the comforts found in our Brewster retreats as well.
The Sea Captain’s Town
The seas that surround our island home have also been the source of many employment opportunities, and Brewster especially is known for its seafaring characters, including the many (50+) sea captains who resided within its city limits. Today, some of the sea captain’s homes still remain standing, and a few have been made into museums that are popular attractions, offering a glimpse into the time period and the life of those who made their living from the sea. The most well-known sea captain home, the Captain Elijah Cobb House: Brewster Historical Society Museum, is located at 739 Lower Road and is a reminder of one of our most famous sea captains, Captain Elijah Cobb. Known for his world travels and for his visit to France during the revolution, where it is reputed that he met with and later witnessed the execution of Robespierre. During the war of 1812, he was a prisoner of war after his ship was captured and was returned home in a prisoner exchange. Today, his home is not just a museum, it is also the headquarters for the Brewster Historical Society, offering six exhibit galleries. The museum is open on Saturdays from noon until 3 PM through October.
More Historic Homes
Brewster was first settled in the mid-1600s, and although few homes remain from those earliest days, there are more than a few historic homes that have been rescued, renovated, and can be toured today, as listed below.
Crosby Mansion, 163 Crosby Lane
The Crosby Mansion is an impressive piece of architecture, having started out as a simple middle-class home until its owner, Albert Crosby, expanded the structure, wrapping it in a much larger and more opulent fashion. Making his fortune in distilled alcohol for medical purposes during the Civil War, he returned to Cape Cod with a bride that was 20 years younger. Today, the extravagant mansion, featuring parlors that were based on the Palace of Versailles, Buckingham Palace, and included a 60-foot viewing tower, is maintained by the non-profit organization Friends of Crosby and is open for guided tours in July and August. The gardens are open to the public all summer long, inviting visitors to one of the more relaxing things to do in Brewster. Stroll about and relax in peace, quiet, and the fragrance of the flowers that have grown in these spaces for over 100 years.
Stony Brook Grist Mill, 830 Stony Brook Road
The Stony Brook Grist Mill was the first business in Brewster, originally built in the 1600s, although the structure standing in its place today was constructed in 1873 on the foundation of an old fulling and woolen mill. Today, the grill is in operation still and visitors can purchase its corn meal taking it to their Pretty Picky Properties fully equipped kitchen to make authentic corn bread, as well as explore the museum that tells the story of that industrial era in Brewster. Open on Saturdays, June through August.
The Events That Make Brewster Stand Out
We have always felt that the best way to get to know the place you are visiting is by attending the festivals and events that the locals love and Brewster offers a few special festivals that we look forward to all year long. We’ve listed our favorites in this Brewster guide.
Brewster in Bloom, Early May
Winters can be harsh, making us appreciate the warmer weather of spring and Brewster in Bloom, held every May for 30+ years (38 in 2024) pays homage to these warmer days. Offering live musical performances, arts and craft fairs, even a Cape Cod 5 Bloom Run, in addition to all the beautiful flowers that will be seen throughout, we think our favorite part of this festival is the Brewster in Bloom Town Parade, held on Sunday morning. Also, in celebration of the festival, various businesses will be having their own special events, including Garden Design classes at Cape Cod Museum of Natural History, book signings at the Brewster Book Store, and a chowder tasting at JT’s Seafood Restaurant.
Brewster Summer Arts & Craft Festival, July, Drummer Boy Park
The most beautiful places on earth attract the most talented artists in the world and in July, the two combine to create the Brewster Summer Arts & Crafts Festival, much to the delight of visitors and locals alike. Offering over 100 booths that display masterpieces from all art genres, including painting, photography, pottery, and jewelry, it also provides skin care products, made from scratch baked goods, and a variety of other food related wares that will add taste to your cooking experiences. There will also be crafts demonstrations for those who would like to learn how to make some of the crafts they see for themselves, perhaps not having to worry about carrying the pieces they love in suitcases that may already be over full. Admission is free and leashed pets are allowed to join these things to do in Brewster.
Brewster for the Holidays, December, Lemon Tree Village
If you want to enjoy a traditional white Christmas, visiting Brewster during December will definitely help you regain your holiday spirit, with Brewster for the Holidays celebrating over many days in early December offering Christmas carolers in period garb strolling through the streets of Brewster, holiday band concerts, and even a tree and windmill lighting ceremony that you won’t find anywhere else.
Natural Adventures in Brewster
The first vacationers landed on our Cape Cod shores at least 400 years ago, drawn by the natural beauty they found there and in Brewster, that natural land and seascape is still a very large draw. Offering sandy shores, sea views, and all manner of natural attractions, playing outside may be your favorite way of enjoying your escape to the Cape and the spots listed below are highly recommended.
Brewster Flats
The definition of tidal flats, a level muddy surface that borders an estuary, exposed when the tides retreat, really doesn’t describe the magic that can be found there, especially in the Brewster Flats. Offering over 12,000 acres at low tide, they are actually the largest tidal flats in the nation, and their charm lies in the marine life that is exposed in that mud, lingering in puddles of water and providing a glimpse into the world that lies under the sea. Crabs, clams, snails, fish, even starfish may be found in those exposed areas, delighting children and adults. Many of our oyster farms are located on the flats, oysters that you can enjoy at many local restaurants, and seeing where they get their start is always a fascinating experience.
Nickerson State Park, 3488 Main Street
Offering 2000 acres of kettle ponds, hiking trails, bike paths, and more, spending at least one of your vacation days exploring Nickerson State Park is destined to be an excellent idea. Most of the trails will take you to and around the kettle ponds, with the Cliff Pond Trail being one of our favorite easy trails, leading hikers around the pond and through wooded areas. The pond itself is known for its clear waters, making it a popular swimming hole on a warm summer’s day. The park also offers picnic tables, basketball courts, and a playground with swings, offering fun for visitors of all ages, but there is a fee for non-residents, so be prepared to pay.
A Taste Tour of Brewster
Although our Pretty Picky Properties kitchens encourage guests to enjoy at least a few meals “at home,” the best part of vacation life can be enjoying the flavors of the towns you are visiting, and we would never want to deprive our guests of that joy. The restaurants listed below are just a few of our favorites; be sure to bring your appetite, because most of these places offer hearty meals!
The Kitchen Café Brewster, 2671 Main Street, Closed Tuesdays & Wednesdays
Originally a restaurant based out of Boston, the Kitchen Café moved to Brewster after the pandemic and the owners never looked back, something we are entirely grateful for. Open for breakfast and lunch, (8AM-2PM) and offering a menu filled with classic breakfast favorites, we are obsessed over their sweet cream pancakes and can’t get enough of their Morning Glory Breakfast Sandwich made with two eggs, choice of meat, cheese, hashbrowns, and chipotle aioli, it offers a spicy start to our day. Their lunch menu features a large selection of sandwiches, but if you are still in the mood for breakfast, their breakfast burrito takes the number one spot!
JT’s Seafood Restaurant, 2689 Main Street, Open Seasonally
JT’s Seafood Restaurant is a local favorite that closes for the winter months, but summer visitors enjoy their extensive menu of seafood delights, including their famous lobster rolls and “chowdah.” Also featuring 20 flavors of ice cream, this local hot spot is a part of our summer tradition.
Laurino’s Tavern, 3668 Main Street, Closed Sundays
We believe that pizza is the international food language of love, and the pizzas and classic Italian meals served at Laurino’s Tavern has been proving us right for over 50 years. Family owned and offering a place for families to feel comfortable as they enjoy a hearty meal, this eatery may be one you return to over and over again.
Pretty Picky Properties Brewster Retreats
As we mentioned earlier, each of the towns and villages that make up Cape Cod all have their own distinctive personalities and vibes, and our Pretty Picky Properties Brewster retreats will reflect the personality of the town. Coming in a variety of styles and offering as many as six bedrooms and as few as two, travelers can choose a beachfront cottage with the sea in their backyard, a family home with a private pool in the backyard, and everything in between.
Amenities Make the Difference
Not every vacation property management company understands the importance of amenities, but our luxurious escapes are filled with the extras that make travel fun. In addition to private pools and beachy views, the property you choose to make your own will offer an extensive list of amenities; gas fireplaces in the living rooms and occasionally in the bedrooms, state of the art televisions, and stunning kitchens filled with name brand appliances, stone countertops, and lobster pots, because, well, you are on Cape Cod and that’s how we roll! Add romance and warmth to a chilly night when you submerge yourself in the bubbly waters of a hot tub under the stars or gather round the firepit roasting marshmallows for s’mores while telling the scariest of ghost stories. Game rooms with pool tables and arcade games, spa-like bathrooms with steam showers and soaking tubs, and the ability to bring the entire family on vacation in our pet friendly rentals.
We work hard to make sure your Cape Cod adventures are comfortable, luxurious, and unforgettable. Reserve your favorite Pretty Picky Properties Brewster sanctuary today and spoil yourself in all the ways that matter.
