Penelope of Is This Seat Taken? is giving us an inside look into Cape Cod!
I grew up “on the Cape” during the summers. My happiest memories are biking to the beach, jumping in the car for ice cream, or taking the boat to the local Clam Shack. My knees were skinned, my hair salty, my pockets filled with oyster crackers.
It was summertime perfection!
As an adult, I now appreciate the fine-dining, music venues, and historic homes. But the charm and nostalgia of the seaside bike trails and quaint marketplaces are likely why families, couples, and friends return every year. I always look forward to being back on “Cape time.”
Here’s my local’s guide to visiting Cape Cod!
The Best Time to Visit
During the summer the hydrangeas are in full bloom, outdoor seafood shacks are booming and the waterfront shores are lively. Calendars can fill up quickly with concerts, baseball games, and community events.
Though everything is at its peak from June through August, this is also when tourists take over. September and October are still warm, but the traffic tapers off and the activities and attractions are more accessible.
Even during the summer, the weather tends to be cooler on the Cape, so packing a jacket and wearing layers are always recommended!
You will definitely want a car if you travel to the Cape and to explore different areas! There are car rental places by the Hyannis airport and most of the larger towns.
Cape Cod has 15 towns and is usually defined as Upper Cape, Mid-Cape, Lower Cape, and Outer Cape.
Heads up: It’s almost impossible to visit them all in one trip.
Provincetown is the one exception for not needing a car. The Bay State Cruise Company and Boston Harbor Cruise ferries go directly from Boston to “P-Town” and it’s easy enough to spend a weekend there.
Where to Stay
White Wind Inn is a renovated Victorian mansion with original woodwork and nautical details preserved from 1845. The Inn is located on Commercial Street in Provincetown, so guests are right in the middle of the hustle and bustle. The rooms are comfy, the owners are accommodating and the porch is ideal for people watching.
Chatham Bars Inn is the picture-perfect setting for a Cape Cod stay. It also has all of the amenities: pool, tennis courts, golf course, and restaurants on site. CBI’s private beach is full service and there is even a boat shuttle that will take you on a harbor tour or drop you off at North Beach Island just across the cove.
If you don’t stay here, you can still experience their Clambake Dinner, a beach tradition with locally caught seafood.
The Escape Inn is a clean and minimalist hotel in South Yarmouth. It’s a reasonable rate and within driving distance from all the Cape has to offer!
Wood’s Hole Inn is a B&B that is all about the personal touches. It’s been recently remodeled so the rooms have the Cape Cod charm but also modern bathrooms. Their scrumptious breakfast will have you ready to ride the Shining Sea bike trail or hop on the ferry, both located just steps away.
Local Highlights in Outer Cape
Sitting at the northernmost tip of Cape Cod, Provincetown boasts miles of beautiful white sandy beaches. The two most notable have very different landscapes. Race Point features dunes, surfer waves, and sea life, meanwhile, Herring Cove on the bay side promises calmer waters.
Commercial Street is the center of town with art galleries, boutique stores, and some beautiful houses and gardens. Though it sounds peaceful, P-Town also has the distinction of being home to the LGBTQ community and it can get a little rowdy!
For a slightly edgier experience, make sure to stop by one the drag shows or cabaret performances. Peregrine Theatre Ensemble is Provincetown’s version of Broadway. Celebrities often stop by, host, and test out new projects on these stages.
Visitors should absolutely rent a bike to explore the area! Province Lands Trail is 5.25 miles of all the sights: dunes, marshlands, and cranberry bogs. For getting out on the water, the Dolphin Fleet provides the best whale watching tours.
From Provincetown, it’s a short drive to Truro, which is largely undeveloped. There is a small winery, which has a tasting room and picnic tables.
My other recommendation would be a short hike up Bearberry Hill, which overlooks the Atlantic Ocean, Pamet River Valley, and Ballston Beach. It looks like the setting of a romantic comedy!
Beachcomber in Wellfleet
Stop by Wellfleet
The next town over is Wellfleet. Definitely treat yourself to an afternoon at the Beachcomber, a restaurant perched on a high dune overlooking the ocean and Cahoon Hollow Beach. The food is standard New England fare, so it’s the beach party ambiance you go for.
There is also a fun drive-in movie theatre here that runs double features during the summer. During the day it is the host of the longstanding Wellfleet Flea Market which has over 200 vendors (most are cash only!).
During the week it can be a bit of a dud, but the weekends can unearth all sorts of treasures. The town itself is small with galleries, farm stands, fish markets, and marshland walking trails.
Local Highlights in Lower Cape
Chatham is the perfect place to stay for a more refined Cape experience.
The town has beautiful beaches, golf courses, high-end fashion boutiques, and chic restaurants. This is a great place for visitors who want the quintessential Cape aesthetic, recreational activities, and a relaxing vacation.
The main public beach is Lighthouse Beach. After walking down the stairs from Chatham Light, go right and walk along the ocean.
You’ll pass the spooky Chatham South Beach Shack, an art project made of driftwood and other washed-up materials.
This will lead to a calm inlet with sandbars during low tide. Since there are no amenities here, it keeps the beach from becoming overcrowded.
Pack a picnic to take advantage of the day!
Just next to Lighthouse Beach is Monomoy National Refuge with trails that wind around dunes and marshes. It’s the prime viewing spot for birds and seals.
More recently, tourists travel to the area hoping to see the “summer home of the Great White.” Just to be safe, the beach warning signs now depict a shark and come attached with an emergency blood-loss first aid kit.
Lower Cape offers wildlife boat excursions too. Though the birds and seals are described as the main attractions, most tour guides will be on the lookout for sharks.
Local Highlights in Mid-Cape
Staying in Mid-Cape gives you the advantage of being within an hour’s drive (without traffic!) of pretty much everything. These towns have fewer hotels, and instead are jam-packed with motels and inns. An alternative option is renting a house or cottage within walking distance to a beach.
Hyannis is the main mid-Cape town with nearly 70% of the population residing here. It can get crowded and lacks New England quaintness. On the “pro side” are the airport and ferry terminals, and boat excursions that leave from the Harbor.
Deep-sea fishing, sunset cruises, or catamaran tours are offered daily during the season. It is also home to the famous Kennedy Compound which is mostly obscured from the street and nearby Hyannisport beach. Instead, there is a well-regarded museum and self-guided legacy trail that you can follow in town.
To get away from the crowds, head to the northern side of the Cape. Gray’s Beach is a small bayside beach with a picnic area and boardwalk. During low tide, the sandbars can stretch all the way to the island across the way. If this beach is full, Mayflower Beach and Corporation Beach are nearby favorites as well.
Food + Entertainment
A lesser-known Mid-Cape town Is Osterville. The main street is a great destination for lunch or dinner. If you drive along South Main Street you will also be rewarded with views of the nicest waterfront homes in Massachusetts.
For entertainment, the Cape Playhouse and Melody Tent are small venues that draw in a surprising amount of celebrities and well-known artists. Nearby West Yarmouth is where the incredible mini-golf courses are located, including the legendary Pirate’s Cove.
Local Highlights in Upper Cape
If you want a more authentic Cape experience, head to North Falmouth and Wood’s Hole. This Upper Cape area has activities and attractions without the crowds and tourist traps.
Old Silver Beach is a nice beach day option with white sand and warm, shallow water. If you’re not watching the sunset at this beach, plan an after-dinner walk to The Knob, a picturesque peninsula that extends into Buzzards Bay.
The absolute best way to see the Upper Cape is via the Shining Sea Bikeway path that stretches from North Falmouth to Woods Hole. This 10.7-mile former railroad path features bird sanctuaries, marshes, forests, cranberry bogs, and sea views.
Check Out Wood’s Hole
The striking Nobska Light is located at the tip of Wood’s Hole. On a clear day, you can see the Islands from here! The Wood’s Hole harbor is where magnificent sailboats and schooners like the Liberté dock. A day sail is an unforgettable experience and every trip is different depending on the wind!
From the harbor, it’s also an easy ferry ride to Martha’s Vineyard and Nantucket.
Wood’s Hole is home to some of the world’s most esteemed marine and environmental science centers. The Marine Biological Laboratory offers free tours and the Oceanographic Institution Discovery Center is both child and adult-friendly.
To show off some of your new marine knowledge head just 20 minutes south to Waquoit Bay. This hidden gem has forestry trails, beach walks and a shallow bay for kayaking. You can also paddle to Washburn Island which is one of the largest undeveloped sites on the Cape.
Things You Have To Eat
Lobster, fried clams, oysters on the half shell, clam chowder, and fish and chips are all worthy dishes on Cape Cod.
Really anywhere that offers fresh seafood is likely good. For a bona fide experience, stop by one of the local markets and have a seafood feast at home or on the beach! Chatham Pier Fish Market, Mac’s Seafood, and Falmouth Fish Market carry only the best so all you have to do is prepare it!
Massachusetts, and especially Cape Cod, is responsible for most cranberry production. There are bog tours located throughout the Cape if you want to learn more or see the harvesting first hand.
Because of this, you’ll find cranberries in pastries, pies, and ice cream. One of my favorite ways to embrace the cranberry is with First Crush Winery’s Cranberry Wine Slushie available in the warmer months.
Cape Cod mudslides are also particularly good with some ocean air and waterfront views. The Chart Room and Baxter’s excel at these chocolaty concoctions. Word to the wise: they are definitely stronger than they appear!
Restaurants You Must Try
Pie in the Sky in Wood’s Hole is an exceptional bakery and produces some of the best pastries on the Cape. Get there early because items sell out quickly!
Hanger B is a no-frills brunch spot in Chatham. Their menu is seasonal but the cult favorites include the Lemon Ricotta Pancakes and the Huevos Rancheros Tacos.
The restaurant is located at the Chatham Municipal Airport so you can watch the Cessnas and Biplanes take off. If you want a bird’s eye view of the Cape, the airport also offers tours!
For Ice Cream
New Englanders love their ice cream so there are options everywhere you go. My favorite is Four Seas in Centerville.
The store has been serving homemade ice cream since 1934. They have the honor of accidentally creating “chip chocolate” ice cream: melted chocolate that solidifies when it hits the frozen ice cream.
For Lunch or Dinner
The Raw Bar is located in the Popponesset “Poppy” Marketplace. I grew up spending my summer days here but there is also an adults-only bar and restaurant hidden in plain sight. Locals come for the lobster roll and quahog but stay for the vibe.
Glass Onion is just off the main street in Falmouth and is my recommendation if you’re looking for an upscale experience and romantic setting.
For a more casual option, Añejo is down the street and has perfected the tableside guac, lobster enchiladas, and margarita.
CRISP is a newer addition in Osterville but quickly has become a fan favorite. Order a salad and pizza to eat inside or enjoy on their patio with lawn games and a firepit.
Captain Parker’s Pub is located on a busy street in West Yarmouth. A lot of restaurants here are marketed for tourists but this place is the real deal. Go for the clam chowder and fresh seafood.
THE red INN was built in 1805 and offers seasonal indoor and outdoor dining. This is the place to be in the afternoon when they are serving their Raw Bar Happy Hour menu. It’s also on the same beach that the Pilgrims first landed in the country (yes, that is why there is a Pilgrim Monument!).
For an alternative, The Club is located on Commercial Street and near all the action. The restaurant has a great outdoor view, friendly staff, and lively interior (picture neon pink walls, illuminated dance floor, and live band.)
Chatham is not known for its nightlife, but the local watering hole on Main Street is the Chatham Squire which is the best place for a beer, cup of chowder, and some live music.
Don’t drive if you are within walking or biking distance to the beach. The lots can fill up quickly during the summer and the parking fees can be as much as $30.
Check the Cape Cod Online events calendar before your trip. There are Cape Cod Baseball Leagues, farmers’ markets, community concerts, and festivals happening all the time!
If you have time, a trip to Martha’s Vineyard or Nantucket should definitely be on your to-do list! There are ferries that travel there from both Hyannis and Wood’s Hole.
For more planning tips check out my highlights of Cape Cod, Martha’s Vineyard and Nantucket, and this 7-day Cape Cod and Islands itinerary!