September And October Are Two Of Cape Cod’s Best-Kept Secrets

Those who love Cape Cod’s incredible beaches, alfresco restaurants, art galleries, and boutiques know that summer doesn’t end on Labor Day. The Cape has a secret season, a second summer that extends through October. Insiders — and the initiated — consider it the very best time of the year to visit. They come for the warm National Seashore sands, glorious Cape Cod weather, and a bevy of art, literary, and food festivals - minus the summertime crowds. The Cape’s legendary Fall season is the ideal time for visitors from all walks of life — and the September waters are at their warmest.

First, where to stay? One property I can recommend is the one where my husband Bill and I personally stay during the summer months. It’s Viking Shores Motel in Eastham, one of many mom-and-pop motels that dot the landscape here in this part of the Cape. Though it is not a luxury property – the Four Points in nearby Eastham, open year-round, is the most upscale property in Eastham and the neighboring town of Wellfleet – Viking Shores is a clean, well-lit family-run, and very family-friendly motel that upgraded some of its rooms last year. It even offers a hearty and complimentary Continental breakfast during July and August — which is very unusual. It may not have frills, but it does have a heated swimming pool in summer, picnic grounds, barbecue grills, and a fire pit, and is ideally located near a wealth of beautiful, award-winning beaches that are a five-minute car ride away. It is also situated right on the Cape Cod Trail, which is perfect for walking, running and biking. Trip Advisor has given this property a 4.0 rating out of 5.0 for “very good,” and I would heartily agree with that. Your kids — and grandkids — will love the fact that a miniature golf course and Poit’s ice cream shop are right next door.

“September is the best time to be at the Cape,” says Viking Shores General Manager Alan Carrier, who advises that the temperatures on Cape are 15 degrees warmer than Boston in late Fall and winter. “Advantages to visiting the Cape in the Fall are that it’s not hazy and humid, and biking and outdoor activities are less exhausting. Our property and our sister property, the Midway Motel in Eastham, are both on the Cape Cod Bike Trail, and it was re-paved last year. Also, last year we swam in the warm bay waters until October 14^th – and the restaurants aren’t overcrowded in September and October.” (Rates at Viking Shores as of September 18^th are $85 a night, $96 on the weekend plus tax.) “We’re much cheaper in the Fall months.”

Of course, I couldn’t write a story about Cape Cod without featuring its beautiful, majestic, dune-filled beaches, many of which, like Coast Guard, which are award-winning. We have been to all of the stunning beaches and they include Nauset Light, Maguire Landing, Marconi, and Newcomb Hollow. Days are perfect for swimming and sunning, while evenings, with a permit, you can have a bonfire on the beach. Afterwards, nothing beats heading over to Nauset Ice Cream, for what we believe is one of the world’s best Cookies and Cream flavors, and trust us — we are connoisseurs of all-things-ice-cream-Ore0.

Restaurateur Todd Barry agrees. A Wellfleet resident – and owner of the famous and uber-successful Moby Dick’s Restaurant, Mr. Barry told me, “Absolutely – Labor Day to Columbus Day is the best time to visit the Cape. The kids are back in school so it’s not busy, the weather is fantastic, and everything is still open and not crowded.” For the record, Moby Dick’s is a great seafood restaurant where you can BYOB and taste the popular lobster roll ($36, served with cole slaw and French fries), and the specially made Key Lime Pie that is shipped right from its maker down South in Georgia. Personally, I always order the broiled scallop dinner that comes with sweet corn and baked potato – a whale of a meal although you can also order other fresh-caught fish and upper-crust crustaceans. ! Moby Dick’s remains open in the Fall until Columbus Day, October 10^th. And right next door to the restaurant, the Moby’s Cargo gift shop is a great place to buy souvenirs of all-things-Cape. All I can say is that when we dine at Moby Dicks’, I’m happy as a clam.

Also in Wellfleet is the incredibly successful PB Boulangerie and Bakery. Owner Philippe Rispoli defied the odds and 13 years ago up an authentic French bistro – in a land known for inexpensive clam shacks. Now open year-round, the PB bakery part of this adorable restaurant, especially, does a booming business all day long. Here's where you’ll find baguettes, semolina bread, cranberry bread with bacon, yummy croissants made with chocolate, and almonds, plus the oh-so-French Croque Monsieur, and all kinds of other sandwiches and pastries. “I work for my customers, and I love like crazy what I do,” Chef Rispoli told me.

The steady stream of customers who line up from 7AM to 6PM daily attest to just how good the goodies are here, including the homemade jams that Philippe’s mother makes by hand, and groceries like you would find at Monoprix in Paris (one of my favorite stores). “We are celebrating 13 years of business in Wellfleet, and next year we will make the restaurant even better.” Yes, there’s a restaurant, which will be re-starting dinner service in November. C’est si bon!

In Provincetown, here are some special events you can partake of this Fall:

ArtProvincetown Festival, October 7-9, 2022

The second annual ArtProvincetown Festival will include museums, galleries, studios, and a marketplace for artists and artisans. The festival welcomes artists, collectors, designers, and art fans of all forms, and it will feature exhibitions, receptions, and parties. The mission of the ArtProvincetown Festival is to highlight the diverse and beautiful art that Ptown is famous for.

Washashore Music & Arts Festival, October 7-9, 2022

The Washashore Music & Arts Festival takes place the same weekend as ArtsProvincetown and is an annual gathering celebrating live music, queer artists, beer, and the singularity of Provincetown. Calling itself “A 3 Day, Town-Wide, Genre-Bending Queer Music Festival,” the event is presented by Provincetown Brewing Co., Crown & Anchor, and Tangle-Made Productions.

Women’s Week October 10-16, 2022

Women’s Week is billed as the ultimate festival in the US to celebrate women. There are more than 150 events scheduled for the week. The highlights include shows, film screenings, dance parties, music, comedy, dune tours, sailing excursions, food events, and sports events. Women’s Week brings thousands of women together—singles and couples alike. As an added attraction, Fox Fest will run October 14-16.

Single Women’s Weekend October 12-15, 2022

The annual Single Women’s Weekend has emerged as a fast, fun way for single lesbians to meet other single lesbians – live and in person, and it’s now a vital part of Woman’s Week.

Fantasia Fair, October 16-23, 2022

Launched in 1975, Fantasia Fair (a.k.a. Fan Fair) is the original transgender event. It offers anyone who identifies as trans (as well as those who don’t) a place to gather. Daily keynote speakers and workshops are features of the busy week-long schedule, filled with fashion shows, formal banquets, lunches, and a cabaret/talent show. It’s an immersive event, considered the longest-running transgender event in the world.

Spooky Bear Halloween Weekend, October 28-30, 2022

Spooky Bear Weekend features parties, dances, a haunted house, a costume ball, and shows. It ushers in the town-wide celebration of Halloween, which may well rank as the most festive and colorful night of the year on Commercial Street.

For more on fall in Provincetown, visit Provincetown Tourism.

All of this makes clear that the line from Patti Page’s famous song “Old Cape Cod, “If you’re fond of sand dunes and salty air, quaint little cottages here and there,” is a year-round tune for many!

For more about my Wanderlust travels, please Follow me on Instagram at @Debbikickham.