One of Cape Ann’s finest beaches, Gloucester’s Wingaersheek Beach is a lovely spot for a rejuvenating beach retreat or sunny getaway. You’ll love the wide sunbathing beach that seems to get longer at low tide. The beach is home to unique rock formations that are fun to explore and a playground for photographers.

When the summer season is high, Wingaersheek Beach is a lively place for sun worshipers who like a sandy beach with plenty of room to spread out. During the shoulder seasons, Wingaersheek is a serene beach where you can stroll and contemplate life.

After a day of soaking up the glorious sunshine, you can have fun on the water, dine overlooking the water, or stroll through downtown Gloucester.

Note: Some information in this article was obtained through a sponsored press trip, but all recommendations are my own.

Sandi Barrette

Toes in the sand time

The best thing to do at Wingaersheek Beach, of course, is to lay down a blanket and soak up the glorious sunshine. Grab your favorite beach novel, some sand toys, and a picnic so you can shake off your work troubles and focus on the job. #beach life.

Along the Annisquam River and Ipswich Bay, Wingaersheek Beach is a popular destination. From Memorial Day weekend to Labor Day, there are lifeguards between 9 a.m. and 5 p.m. to keep your swim time safe. Wingaersheek offers an on-site concession stand and restrooms with showers, providing beachgoers with all the niceties that make a day at the beach enjoyable.

The beach is located outside the main town area so unless you have a rental within walking distance you will have to drive. When visiting during the summer season, you’ll want to plan to spend the whole day at Wingaersheek Beach as parking is chargeable and the parking lot fills up early on a nice day.

Beach entrance.
Entrance to the beach (Photo credit: Sandi Barrett)

Wingaersheek is an ideal beach for a relaxing stroll after the crowds have thinned out. It’s especially nice at low tide when the receding water exposes a long sandbar.

Pro tip: New for the 2022 beach season, Gloucester has launched an online non-resident beach parking reservation system. Yodel, a parking management app, allows non-residents to book and pay for parking at Gloucester beaches up to 10 days in advance, eliminating the first-come, first-served parking system.

Stone formations.
Sandi Barrette

Explore rock formations

Huge boulders juxtaposed with soft sand are perfect for photographers and explorers. These unique rock formations are fun to climb, but can hold a ton of heat from the bright sun. Proper footwear will enhance your rock scrambling adventure.

Pro tip: Out of season, go at low tide to enjoy a less crowded beach. You will be able to find a rocky perch where you can enjoy a peaceful place to soak up the salty air and warm sun.

Whales at Stellwagon Bank.
Whales at Stellwagon Bank (Photo credit: Sandi Barrett)

Get out on the water

One of the best ways to enjoy a visit to Gloucester is to get out on the water.

Cape Ann Whale Watch will take you to Stellwagen Bank for a whale watching experience. The majesty of these incredible mammals is an awe-inspiring experience. Get your camera ready, they’re quick and nimble considering their size.

Harbor Tours offers an Annisquam River tour where you float through the saltwater estuary, admiring beautiful oceanfront homes, beaches, and local waterfowl. The trip offers a perfect view of the water.

Pro tip: If you’re new to whale watching, you’ll find tips and tricks in this whale watching guide.

Stroll through the village of Annisquam

The charming seaside village of Annisquam is a lovely place for an evening stroll. New England-style buildings like the town hall and church in Annisquam anchor the small enclave.

Almost completely separated from the mainland by Lobster Cove, the village is reached by a long winding road, or by the wooden footbridge that spans the pretty cove.

Pro tip: Parking is difficult to find in the village of Annisquam. If you see a spot, don’t pass it by. The village is small and easily accessible on foot.

Fishermen's Memorial.
Sandi Barrette

Explore Gloucester city center

Gloucester city center is a fun place to stroll. You’ll find beautiful ocean views from many places downtown.

The commercial area, just up the beach, is full of unique shops with large display windows displaying souvenir options. A walk around town could yield that elusive decorative item, a collectible fridge magnet, or a cute outfit for your grandkids. It’s just what you need to complete your holiday shopping list.

Be sure to walk down central Stacy Boulevard to see the famous Fisherman’s Memorial. The memorial is dedicated to the thousands of Gloucester fishermen who were lost at sea.

A little further down the street is a monument dedicated by the Fishermen’s Wives Association to honor the women of Gloucester. The poignant Fishermen’s Wives Memorial depicts a woman and her children looking out to sea, waiting for their fisherman to return home safe and sound.

Pro Tip: See our Gloucester visitors guide for more on things to see and do around Gloucester.

Good harbor beach.
Good harbor beach (Photo credit: Sandi Barrett)

Other Area Beaches to Consider

Wingaersheek Beach is a great getaway, but Gloucester has several other great beaches to explore. If you’re staying near one of these other beaches, consider trying another spot to spread your blanket for a day of sun and sand:

  • Good harbor beach
  • Half moon beach
  • Plum cove beach
  • Beach Pavilion

Pro tip: Be sure to check out our comprehensive guide to Gloucester beaches.

1606 Restaurant and Oyster Bar
1606 Restaurant and Oyster Bar (Photo credit: Sandi Barrett)

Where to dine in Gloucester

There is a fine selection of restaurants throughout Gloucester. Many offer fresh catch specialties and local lobster dishes. You’ll find excellent seafood and earthy gifts for your culinary exploration.

1606 Restaurant And Oyster Bar

Hotel Beauport’s beautiful 1606 Oyster Bar and Restaurant is a charming place to dine and has views of Pavilion Beach. The Cape Ann lobster roll is perfectly cooked and served just the way you like it, with butter or dressing.

mile marker one

At Cape Ann’s Marina Resort’s Mile Marker One Restaurant, guests can enjoy fresh-from-the-sea dishes caught off the restaurant’s own lobster boat. Consider an all Gloucester lobster dinner. Start with the lobster-stuffed avocado served with chipotle mayonnaise, roasted corn, salsa and tortilla chips. Lobster mains include creamy lobster mac and cheese, classic lobster roll, or Italian-inspired lobster bruschetta. Mile Marker One is all local, all lobster, all the time – yum!

Set in the heart of the marina and boasting magnificent views, Mile Marker One is a great place to soak up Gloucester’s coastal vibe.

Pro tip: While Wingaersheek Beach has a concession stand for a quick lunch, explore your options for a delicious dinner. Be sure to make reservations to avoid a long wait for a table.

Stunning Beach House Destinations

Ocean View Retreat

Evensong is a beautiful ocean view retreat overlooking the Annisquam River and Wingaersheek Beach. Offering beautiful views and water access for kayakers or paddlers (bring your own), colorful sunsets and waterfowl sightings, you’ll love this relaxing vacation stay. With three bedrooms and two bathrooms, the rental sleeps six and is spacious enough for a small family reunion and comfortable enough for a romantic getaway.

Classic Beach Cottage

If you desire a getaway with ocean views on your doorstep, this classic beach cottage may be the perfect spot. This scenic beach rental is located on the Annisquam River – at high tide the water rises under the bridge. Offering access to Wingaersheek Beach, Annisquam Village and a private beach, drop your bags and sink into your tranquil beach getaway. Imagine sipping on your favorite drink while watching the tide roll in your way. It doesn’t get any better than that.

Local rental agency

Annisquam Village Realty offers a fine selection of vacation rentals in the area. Booking a stay with a trusted local agency gives you the assurance that your stay will be exactly as promised.

Pro tip: Booking a stay within walking distance of Wingaersheek Beach will enhance your Gloucester getaway with ocean views and proximity to all the beach fun. Walking means less time in traffic and no parking fees.

Getting to Wingaersheek Beach

Boston Logan International Airport is the closest major airport to Gloucester. It will take you less than an hour to get to the center of Gloucester when traffic is light – longer on Fridays during the summer.

Road travelers will love the trip from Boston to Gloester. You can make the trip in less than an hour or take your time and explore along the way.

If you don’t want to drive, the train from North Station (this will require carpooling or an additional train from Logan) on the Newbury/Rockport line will get you there while you relax and enjoy the ride.

Pro tip: Gloucester is a popular summer destination. Allow extra driving time during peak hours for weekend getaways.

Wingaersheek Beach.
Sandi Barrette

Stylish Gloucester Beach Getaway

When planning your next sea getaway, add Gloucester’s Wingaersheek Beach to your list of sunny beaches. This charming spot on the North Shore of Massachusetts is a great vacation destination. Gloucester is the perfect place to experience the freshest seafood, explore the unique coastline and fall in love with Wingaersheek Beach.

Explore all that Massachusetts has to offer, including: