Shoulder season, that precious blip of time between high and low tourism seasons, falls between September and late October on the Cape. It's a period where travelers can really make the most of their time in any destination, as it means fewer fellow tourists to contend with, so you get the prime pick of restaurant and hotel reservations and more openings on the hot excursions everyone wants to book. Yes, the air is a touch cooler and the pace is slower, but that just makes every moment feel even more special.

During this secret season, travelers can expect temperatures that hover in the 60s and 70s during the day, which means the beaches are still an inviting proposition under the noon sun. The evenings bring a slight chill, which makes cozying up by a fire, which you'll find in many of the rooms in Forbes Five Star Chatham Bars Inn, all the more enticing.

From quiet beach days and wildlife encounters to art galleries and lighthouse tours, here are the best activities to try out on your next visit to the Cape during the shoulder season.

Stroll Main Street in Chatham

Chatham's Main Street is as charming as it gets, especially as the summer crowds disperse, so you’ll have more elbow space on the sidewalk and can browse its boutiques, galleries, and specialty shops. Pop into the Chatham Candy Manor for small-batch chocolates, peruse the work of local artists at Chatham Fine Art, and pick up cozy coastal-inspired home goods at local shops like Tale of the Cod. Many restaurants along the street stay open through the season and offer outdoor seating so you can soak in those last rays of sun. It's also still a fantastic time to get a lobster roll or bowl of chowder, so go ahead and order both.

Visit the Chatham Lighthouse and Beach

The Chatham Lighthouse has been guiding mariners safely to shore since 1877. It's also one of the Cape's most photographed landmarks, meaning it's a well-visited spot in the high season. And that's why a fall visit is ideal: you can see the Coast Guard–operated station without having to shuffle around too many people, all while drinking in those sweeping ocean views and history lessons all at once. As a bonus, walk across the road to the long stretch of sand for a perfect beach stroll, some birdwatching, or just to spend an afternoon listening to the waves.

Explore Monomoy National Wildlife Refuge

The Monomoy National Wildlife Refuge stretches across more than 7,000 acres and is a haven for migratory birds, seals, and coastal wildlife. By mid-September, the fall migration is in full swing, making this a prime spot for birdwatchers. Travelers can explore the refuge through its vast system of trails that wind through salt marshes, dunes, and beach habitats.

Bike the Old Colony Rail Trail

See even more of the Lower Cape by hopping on a bike for a scenic ride on the Old Colony Rail Trail, which runs eight miles from Chatham to Harwich. The path is connected to the longer Cape Cod Rail Trail, making it easy for avid cyclists to pedal even further if they wish. And, if you time your visit for mid to late October, you'll find the route lined with colorful foliage that makes for a jaw-dropping Instagram backdrop. Chatham Bars Inn offers complimentary bikes for hotel guests through mid-October.

Take in the Cranberry Harvest

Fun fact: Massachusetts harvested 2.26 million barrels of cranberries in 2022, accounting for about one-third of all cranberries grown in the nation. Cape Cod happens to be one of its main growing areas, and September through November also happens to be prime harvesting season. Farms in nearby Harwich, like Leo and Andrea Cakounes' spot, welcome visitors for bog tours and demonstrations of their traditional wet harvest method, giving travelers a serious lesson in where the fruit comes from. Best of all, you get to taste the juice (that's really worth the squeeze) at the end.

Go Whale Watching

Cape Cod is a world-class whale-watching destination, especially in the fall, when the giant marine animals start their migration south for the winter. Travelers can head out on a private whale-watching tour right from the Chatham Bars Inn dock to spot humpback, finback, and minke whales on tours. The knowledgeable onboard crew shares insights into whale behavior as these gentle giants breach, dive, and bubble feed—making for one seriously fascinating, luxurious, and memorable outing.

Explore more secret season destinations across the Benchmark Resorts & Hotels portfolio, a collection of more than 50 distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.