New England Guide: Best Things to Do in Cape Cod & Martha’s Vineyard

“There’s a sunrise and a sunset every single day, and they’re absolutely free. Don’t miss so many of them.”
― Jo Walton

New England Guide

Relax your shoulders, close your eyes and fill your lungs with that refreshing, salty sea air… the Cape in Massachusetts is home to some of the country’s best beaches and is a summer road trip destination that is hard to beat. From boat tours to cruises and mini golf to glass-blowing, the hook-shaped peninsula of Cape Cod will have a little something for everyone.

Perfect for families, couples, and groups of friends, there is enough scenery and seafood in this unique ecosystem to satiate everyone’s palette. Whether you are planning a trip to Cape Cod (the largest), Martha’s Vineyard (the choice of many a celebrity) — or, lucky you, both Atlantic destinations — we’ve got you covered with favourite picks from our local photographer, Caroline in Cape Cod. Ready to get out of Boston and feel that sweet sand between your toes? Let’s go!

Photo: Flytographer in Cape Cod. Bailey and family capture memories in Cape Cod with a family photoshoot.

Cape Cod

When it comes to food, architecture, adorable town centers and beautiful beaches, you can’t beat a Cape Cod summer getaway. While you’re here you need to get a lobster roll from one of the many clam shacks where fresh lobsters are caught daily and try some local fish. Every town has a local art gallery to visit, cute shops and beautiful beaches. Just be sure to follow beach guidelines about sharks! From setting off on a whale-watching adventure to strolling the Cape Cod Rail Trail or from booking a kayaking tour to visiting the heritage museums & gardens, there is quite literally, something for all.

Photo: Flytographer in Cape Cod. Lindsay and partner celebrate a babymoon in Cape Cod with a maternity photoshoot with Flytographer.

Best places to eat in Cape Cod

• Betsy’s Diner (Falmouth): “I have been going to Betsy’s Diner as long as I can remember. This 50s diner is not one to be missed if you love all things vintage. Amazing food from their omelettes to their Belgian waffles, plus gluten-free breakfast options.”
• BŌL (Wellfleet): Gluten and dairy-free smoothie bowls to start your day right! 
• Young’s Fish Market (Orleans): Pick up the freshest seafood here as well as “some of the best lobster rolls you’ve ever had!”
• Cape Cod Creamery (Yarmouth): Make sure to schedule a pitstop for the area’s best ice cream – especially if you are visiting during the hot summer months.

Photo: Flytographer in Cape Cod.Julina and partner capture memories in Cape Cod with a couple photoshoot.

Best places to go for drinks in Cape Cod

• Coffee Obsession (Falmouth): “I am a huge coffee shop enthusiast, so I love stopping in for a latte at Coffee Obsession. Their coffee and tea menu is massive, plus they do offer non-dairy milks and allergy-friendly baked goods. Their Woods Hole location is right by the Steamship Authority ferries so you can grab a drink before hopping on a ride to Martha’s Vineyard.”
• Chatham Bars Inn (Chatham): “Their beautiful display of hydrangea at the front of the inn is a must-see if you are in the area in late July! Go grab a drink down by the water or stay the night if you’re feeling fancy!”

Photo: Flytographer in Cape Cod. Jordan and partner celebrate their engagement in Cape Cod with a couple photoshoot.

Best things to do in Cape Cod

1. Nobska Lighthouse (Falmouth): “There is nothing more nautical than going on a tour of lighthouses around the Cape. Built in 1829, the Nobska Lighthouse in Falmouth has been completely restored. The Keeper’s House will become a Maritime Museum and once the pandemic passes, the Tower tours will reopen to the public.” 
2. Old Silver Beach (Falmouth): “If you are looking for a public beach without needing a beach sticker, Old Silver Beach is the perfect option! It offers beautiful views of Buzzards Bay and has a jetty you can walk along as it juts out into the water. Sitting on the western shore you get amazing sunset views and it provides a great spot to go swimming!” 
3. Shining Sea Bikeway (Falmouth): “Whether you rent a bike or bring your own I love taking a ride on the Shining Sea Bikeway. This 10.7 mile paved bike trail runs along the coast from Falmouth to Woods Hole and boasts beautiful ocean views.”  
4. The Knob (Woods Hole): “The Knob, located in the Cornelia Carey Sanctuary, is a beautiful little peninsula that juts out into Buzzard’s Bay. There is a small parking lot at the end of the dead-end road, but it does fill up quickly. There are multiple trails but when you come to the wooden sign just take the trail on the right the entire way and it will bring you to the Knob. There are small swimming beaches on either side too and a bench at the end to take in the stunning views of the ocean!” 
5. Visit Plymouth: The Mayflower landed in Plymouth, MA in 1620 and today, it is a national historic site located about 40 minutes from Cape Cod along the Cape Cod Bay. Visit the Cape Cod Museum of Natural History or Pilgrim Monument to learn more.
6. Chatham Fish Pier (Chatham): “Watch the commercial fishing boats come in with their catch in the morning and you’ll see a seal or two! It’s cool to watch the fish being unloaded, and then you can walk across the parking lot to the Chatham Pier Fish Market to buy the freshly-caught fish! Great free activity for kids.”

Photo: Flytographer in Cape Cod.

• Nauset Lighthouse (Eastham): “The Nauset Light is a beautiful old lighthouse with a great history. Take a tour, visit the Three Sisters Lighthouses while you’re there and spend the day at Nauset Light Beach. Check your bag of Cape Cod Potato Chips and you’ll see the Nauset Light!” 
• Cape Cod National Seashore: “Created by President JFK, the Cape Cod National Seashore is home to some of the most beautiful beaches on the Cape, from Provincetown down to Chatham. With 40 miles of beach to explore, you can hit a new beach every day and stay on the CCNS!” Visit the John F. Kennedy Hyannis Museum to learn more about the late, former president’s background.
• Grey’s Beach (Yarmouth): “Grey’s Beach has free parking, a big sectioned-off swimming area, boat launch and a long boardwalk that goes right out over the marsh and into the ocean. It is a beautiful spot to explore, take photos and spend the day.” 
• Rock Harbor (Orleans): “Come watch the fishing boats leave in the mornings or charter one of the boats for a day of deep-sea fishing! This peaceful harbor attracts artists who you can find painting along the boardwalk most days. While you’re there, check out Skaket Beach (my pick for best kid-friendly beach on the Cape!) and Young’s Fish Market for some of the best lobster rolls you’ve ever had. Take a photo in front of the Cap’t Cass Restaurant with its iconic buoys.” 
• Crosby Mansion (Brewster): “A beautiful mansion-turned-museum perfect for visiting on a rainy day. The grounds are beautiful, especially during hydrangea season!” 
• Uncle Tim’s Bridge (Wellfleet): “The bridge itself is a beautiful spot to stop and take some photos, but cross the bridge to Hamblen Island and you’ll find walking trails that are perfect for kids. The trails lead out to the beach near Wellfleet Harbor and are not to be missed! While you’re there, stop at BŌL in Wellfleet for the best smoothie bowl breakfast!”

Photo: Flytographer in Cape Cod. Molly and family capture memories in Cape Cod with a family photoshoot.

Best places to shop in Cape Cod

• Commercial Street (Provincetown): “Commercial Street has everything: beautiful homes, shops, history, galleries and great food. Make sure you check out The Lobster Pot for lunch!” – Caroline
• Main Street (Falmouth): “If you are looking for restaurants, gift shops, and local boutiques, Main Street Falmouth covers all your needs. Chocolate enthusiasts, be sure to stop in Ben & Bill’s Chocolate Emporium to fulfill your sweet tooth dreams!”

Photo: Flytographer in Cape Cod. Jacqueline and partner celebrate a babymoon in Cape Cod with a maternity photoshoot with Flytographer.

Martha’s Vineyard

Calling all beachcombers and bike ride enthusiasts! Off the coast of Cape Cod, the small island of Martha’s Vineyard is a hot summer destination for those looking to escape the city and knock some sightseeing off their bucket lists. With upscale shopping, hiking trails, sandy beaches, and the occasional A-lister to spot, this East Coast getaway is an easy sell to the whole family all year-round. Whether you are looking to participate in wine tasting at a local winery, frequent the nearby golf courses, or organize rentals and pedal along the many bike paths to take in the province lands – there is always an abundance of activities to keep you busy in Martha’s Vineyard.

Best places to eat in Martha’s Vineyard

• Larsen’s Fish Market (Menemsha): Don’t miss the lobster rolls and clams fresh from the dock! It’s also the perfect place to watch the sunset.  
• Alchemy (Edgartown): Fine dining at its best.  
• Lookout Tavern (Oak Bluffs): A huge menu of the freshest seafood, including sushi. 
• Artcliff Diner (Tisbury): Cooking up Americana since 1943. Come early to avoid long lines! 
• State Road (West Tisbury): High-end offerings with ingredients straight from the restaurant’s gardens. 
• Scottish Bakehouse (Vineyard Haven): Hearty breakfast fuel-up options at this café bakery.
• Back Door Donuts (Oak Bluffs):  Find the purple door at the back and get in line for sweet treats from heaven!

Photo: Flytographer in Martha’s Vineyard. Sam and partner capture memories in Martha’s Vineyard with a couple photoshoot.

Best places to go for drinks in Martha’s Vineyard

• Behind the Bookstore (Edgartown): Get your coffee here in the morning and your cocktails in the evening in this friendly open-air hotspot.
• The Port Hunter (Edgartown):  Fresh oysters and modern cocktails — need we say more?  
• Bad Martha Brewery (Edgartown & Falmouth): Enjoy a freshly brewed beer in the outdoor garden patio and support the brewery’s efforts to donate profits to a local hunger-relief charity.

Photo: Lucian in Martha’s Vineyard for Flytographer. Taylor and partner celebrate their trip to Martha’s Vineyard with a couple photoshoot. 

Best things to do in Martha’s Vineyard

• Lighthouse Beach (Edgartown): Miles of soft golden sand surround the iconic black and white Edgartown Lighthouse, one of five historic lighthouses on the island.
• Lucy Vincent Beach (Chilmark): Formerly known as Jungle Beach, this is one of the most popular hangout beaches, with a nude beach section at the far end for the adventurous and free-spirited. 
• Gay Head Lighthouse (Aquinnah): The lighthouse’s interior is closed for now due to COVID precautions, but you can still enjoy the incredible views of the clay cliffs, designated a national landmark.
• Lobsterville Beach (Aquinnah): A perfect stretch for a day of fishing, leisurely walks on the sand, or letting the kids run wild.
• The Carnegie (Edgartown): Get your fill of island history surrounded by the beauty that is the newly-renovated Neoclassical former home once owned by the Carnegie family.
• The Campground (Oak Bluffs): Enjoy a stroll around this famous area to get your Insta-worthy snaps of the island’s unique and utterly charming gingerbread cottages.  
• Island Alpaca Farm (Vineyard Haven): Visit a family-friendly alpaca farm — new babies arriving this summer!

Photo: Flytographer in Martha’s Vineyard. Allie and family capture memories in Martha’s Vineyard with a family photoshoot.

The best places to shop in Martha’s Vineyard

• Portobello Road (Edgartown): Book lovers rejoice! The sweetest bookshop that offers accessories and gift ideas. You won’t escape empty-handed.
• Slate (Edgartown): Look for the cheery striped awning that will lead you to a treasury of unique and local fashion finds.
• Alley’s General Store (West Tisbury): The oldest retailer on the island with a post office and all the supplies you could possibly need. 
• The Allen Farm Sheep and Wool Company (Chilmark): A family-run farm offering beautiful handmade preserves, woollens and meat.  
• North Tabor Farm (Chilmark): Gorgeous bouquets of flowers and baskets of fresh fruit and veg are grown and sold at this family farm stand. 

Photo: Flytographer in Martha’s Vineyard. William and family capture memories in Martha’s Vineyard with a family photoshoot.

Capturing memories in New England

Are you inspired to make memories on a day trip to New England yet? Whether you are flying solo or trekking the whole crew with you, one of our amazing, local photographers are looking forward to meeting you in Cape Cod and Martha’s Vineyard. Happy beachcombing and memory-making!