People return to Cape Cod each year for vacation, and many families have been summering here for generations. But have you ever wondered what the Cape might have felt like 50 or 100 years ago? Luckily, many places have either been around virtually unchanged for that long (or longer!) and others that have worked hard to preserve that timeless feeling. Step back in time and experience the best of Nostalgic Cape Cod by visiting some of our favorites!
The Brewster Woodshed (1193 Main St - Brewster)
Originally opened in the 1960s, this bar is a local institution. In the summer, they have live music almost every night (sometimes with multiple acts!), making it a vibrant and lively destination after more family-friendly locations close for the evening.
The Cape Playhouse (820 Main St - Dennis)
Housed in a c.1790 Meeting House that reopened as a theater almost 100 years ago in 1927, this Playhouse is the oldest continuously operating summer theater in America. It saw the stage debuts of such legends as Henry Fonda and Bette Davis in 1928, and came to be called “the place where Broadway goes to summer” by the New York Times. Doris Day, Humphrey Bogart, Julie Andrews, Bernadette Peters and Betty White are among the many Hollywood stars who have graced its stage over the years. Each season (June - Sept) it puts on a half-dozen incredible shows with first-rate talent, and is well worth a visit.
Chatham Orpheum Theater (637 Main St., Chatham)
Chatham’s first movie theater opened in 1916. It operated for 72 years until it shut down in the late 1980s, briefly becoming a CVS, before officially reopening as a state-of-the-art 2-screen nonprofit theater in 2013. In addition to the latest blockbusters, visitors can enjoy film festivals, screenings of locally relevant favorites such as Jaws and The Finest Hours, and free programming for kids and families. Don’t miss the lobby mural by Hans de Castellane, which has 122 Hollywood actors, characters, and personalities.
Wellfleet Drive-In Theater (51 State Highway 6A, Wellfleet)
This classic drive-in, established in 1957, is the last one on Cape Cod and one of only 300 still in existence in the U.S. Watch a double feature each night starting at sunset, rain or shine. Park in the assigned area for your type of vehicle (assigned to ensure that everyone can see!), tune your car radio to 89.5FM, and enjoy the movies! There’s also a snack bar in the middle with popcorn, ice cream, burgers, and candy, among other options. Note that admission is now charged per person (not by car, as was once traditional).
Tip: Instead of the car speakers, you can lower your car windows and listen to the original 1950s speakers outside, which have individual volume controls.
Bonus Tip: Bring lawn/beach chairs (ones that are higher off the ground are better) to set up a seating and picnic-style area outside of your car.
The Cape Cinema (820 Main St - Dennis)
Next door to the Playhouse, the Cinema opened in July 1930 with state of the art technology inside, a relatively simple facade in ode to the traditional Cape architecture, and the largest interior artwork ever created at the time (a mural still visible on the ceiling today). In 1939 it was the site of the premiere of The Wizard of Oz, and was known as “the world’s most beautiful motion picture theater.” Today they play a carefully curated mix of Hollywood films, live concerts, ballet and documentaries.
Bud’s Mini Golf (9 Sisson Rd, Harwich Port)
There are many, many mini golf courses across the Cape, and this is one of our favorites. From the paper score cards and mini pencils to the lighthouse and waterfall hurdles, mini golf hasn’t changed much since the 1950s. Bud’s course is immaculately manicured, featuring holes that work for players of all levels, and can easily be combined with ice cream (check out nearby Sweet Izzy) and/or go-karting at the course next door.
The Pie Stand (403 Main St, Dennis)
Quite simply, Becky and her family make The Best Pies you will ever eat. Operated out of their home Thursday - Sunday in the summer, they offer an extensive list of flavors, all of which are spectacular and come still-warm and wrapped in newspaper. Sea Meadow Inn favorites include strawberry rhubarb and peach ginger!
Tip: Order your favorite in advance by phone and pick up at 1 pm, or show up at noon to choose from their flavors of the day.
Bonus Tip!: Buy their cookies as well. Only sold as an add-on to the pies, these enormous cookies are also spectacular.
Four Seas Ice Cream (360 S. Main St, Centerville)
A Cape Cod institution since 1934, Four Seas is also the oldest ice cream shop in Massachusetts. The line is often out the door of this tiny old-school diner, but it moves quickly and allows you to debate which flavor to get. Try one of the flavors that have been in circulation since the very beginning, add their famous hot fudge, and then take a picture under the neon sign. You won’t regret it!
Tip: All ice cream flavors are home made, with some like Cantaloupe and Fresh Peach (Jackie Kennedy’s favorite!) only made when the fruits are in season.
Brewster General Store (1935 Main St, Brewster)
Originally built as a church, it has been operating as a general store for 160 years (since 1866) under the guidance of just 5 families. Open year round 7 days a week, it has a remarkable assortment of merchandise for locals and tourists alike. From daily newspapers to penny candy, books on local history to coffee, fudge and everything in between, visitors will marvel at the variety.
Tip: Locals often congregate early in the morning to share their coffee while sitting on the benches outside.
Wellfleet Flea Market (51 State Highway 6A, Wellfleet)
As many as 150 vendors set up tables and tents on the drive-in parking area during the day to sell everything you can imagine. From Cape Cod memorabilia to clothing, artisanal items, collectibles and antiques, you can find pretty much anything.
Tip: Bring cash to pay for both parking (a few dollars) and the vendors, many of whom don’t take cards. There are ATMs on site in case you forget.
Dennis Village Green (Rt 6A, Dennis)
From the historic cemetery to boutiques and the large gazebo at the edge of the park, a stroll through the Dennis Village Green takes you back in time. Can’t-miss events include the Dennis Union Church annual auction & bazaar in early August, weekly outdoor live concerts in the gazebo, guided cemetery tours and more.
Tip: The iconic Dennis Village gazebo is featured in a painting by local artist Karen North Wells, which is currently on display on the ground floor of the Sea Meadow Inn.
Dune Shacks Trail (Provincetown)
This relatively strenuous trail across the ocean dunes of Truro and Provincetown leads to the 19 remote shacks, which are a protected historic district and primitive artist residences. Created as lifesaving huts in the mid-19th century, they were converted to tiny homes between the 1920’s and 50s, and are famous for having hosted writers and authors such as ee cummings, Eugene O’Neill, Jackson Pollock, Tennessee Williams, and Jack Kerouac, among others.
Tip: There is no official trailhead or parking entrance to the trail. On your way into Provincetown, you’ll notice cars and bikes apparently parked ‘for no reason’ at the entrance. It’s also marked on our Google map.
About the Sea Meadow Inn: A boutique, 7-room bed and breakfast located in Brewster (inside the ‘elbow’ of Cape Cod). The Sea Meadow Inn was originally built c. 1780 by sea captain Isaiah Clark. In addition to being a private residence, it has operated as a Bed & Breakfast, Inn and even a Tea House at various times since the 1980s. Today, we are focused on providing luxury accommodations, delicious garden-to-table breakfasts, and a peaceful oasis for visitors to rest and recharge energies. Whether you are an annual Cape visitor or exploring it for the first time, we want to help you make the most of your trip.
Looking for information on a topic not included here? Just ask! Perhaps we’ll include it in a future post.
You can also refer to our ever-growing google map of recommendations, which includes restaurants, beaches, thrift stores and so much more!