One of the best beaches on Cape Ann, Gloucester’s Wingaersheek Beach is a delightful spot for a rejuvenating beach retreat or sun-filled getaway. You will love the wide tan beach that seems to go on and on at low tide. The beach is home to unique rock formations that are fun to explore and are a photographer’s playground.
Videos by TravelAwaits
When the summer season is high, Wingaersheek Beach is a bustling place for sun worshipers who love a sandy beach with plenty of room to spread out. During the shoulder seasons, Wingaersheek is a serene beach where you can walk and contemplate life.
After a day of soaking up the gorgeous sun, you can enjoy some on-the-water fun, dine with water views, or enjoy a stroll in downtown Gloucester.
Note: Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.
Toes-In-The-Sand Time
The best thing to do at Wingaersheek Beach, of course, is stake out a blanket spot and soak up the brilliant sunshine. Grab your favorite beach novel, sand toys, and a picnic lunch so you can cast away your work woes and focus on the #beachlife.
Running along the Annisquam River and Ipswich Bay, Wingaersheek Beach is a popular destination. From Memorial Day weekend through Labor Day, there are lifeguards between 9 a.m. and 5 p.m. to keep your swimming time safe. Wingaersheek offers an on-site concession stand and restrooms with showers, affording beachgoers all the niceties that make spending a day at the beach comfortable.
The beach is located out of the main area of town, so unless you have a rental within walking distance, driving is required. When you visit during the summer season, you will want to plan to spend the whole day at Wingaersheek Beach since there is a fee for parking and the lot fills up early on a beautiful day.
Wingaersheek is a great beach for a relaxing walk after the crowds have thinned. It is particularly lovely at low tide when the retreating water exposes a long sandbar.
Pro Tip: New for the 2022 beach season, Gloucester launched an online non-resident beach parking reservation system. Yodel, a parking management app, allows non-resident beachgoers to reserve and pay for their parking space at Gloucester beaches up to 10 days in advance, eliminating the first come, first served parking system.
Explore The Rock Formations
The enormous boulders juxtaposed against the 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 brilliant sunshine. Appropriate footwear will enhance your rock scrambling adventure.
Pro Tip: During the off season, visit at low tide to enjoy a less crowded beach. You will be able to find a rocky perch where you can enjoy a peaceful spot for soaking up the salty air and warm sun.
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 out to Stellwagen Bank for a whale-of-a-tale experience. The majesty of these incredible mammals is an awe-inspiring experience. Have your camera ready, they are quick and agile considering their size.
Harbor Tours offers an Annisquam River Trip where you will float through the saltwater estuary viewing gorgeous ocean front homes, beaches, and local water birds. The trip offers a picture perfect view from the water.
Pro Tip: If you are new to whale watching, you can find tips and tricks in this whale watching guide.
Stroll Annisquam Village
The charming seaside village of Annisquam is a lovely spot for an evening stroll. The New England-style buildings, like the Annisquam Village Hall and Church, anchor the small enclave.
Almost completely separated from the mainland by Lobster Cove, you can access the village by a long, winding road, or by the wooden footbridge spanning the pretty cove.
Pro Tip: Parking is difficult to find in Annisquam Village. If you see a spot, don’t pass it by. The village is small and easily walkable.
Explore Downtown Gloucester
Downtown Gloucester is a fun spot to walk around. You will find beautiful ocean views from many downtown locations.
The shopping area, just up from the beach, is full of unique stores with wide windows displaying souvenir options. A stroll through town might yield that elusive decor item, collectable fridge magnet, or sweet outfit for your grandkids. It’s just what you need to complete your vacation shopping list.
Be sure to walk down central Stacy Boulevard to admire the famous Fisherman’s Memorial. The memorial is dedicated to the thousands of Gloucester fishermen who have been lost at sea.
A little farther 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 portrays a woman and her children looking out to sea, waiting for their fisherman to return home safely.
Pro Tip: Check out our Gloucester visitors guide for more to see and do around Gloucester.
Other Area Beaches To Consider
Wingaersheek Beach is a beautiful getaway, but Gloucester has several other lovely beaches to explore. If you are staying near one of these other beaches, consider trying a different place to spread your blanket during a day in the sun and sand:
- Good Harbor Beach
- Half Moon Beach
- Plum Cove Beach
- Pavilion Beach
Pro Tip: Be sure to check out our full-length guide to the beaches of Gloucester.
Where To Dine In Gloucester
There is a nice selection of restaurants throughout Gloucester. Many offer fresh catch specials and local lobster dishes. You will find excellent seafood and gifts from the land for your dining exploration.
1606 Restaurant And Oyster Bar
The gorgeous 1606 Restaurant and Oyster Bar in the Beauport Hotel is a lovely spot for dinner and has a view of Pavilion Beach. The Cape Ann lobster roll is perfectly cooked and served the way you like it, with butter or dressing.
Mile Marker One
At Mile Marker One restaurant at the Cape Ann’s Marina Resort, you can dine on fresh-from-the-sea fare caught on the restaurant’s own lobster boat. Consider an all-Gloucester lobster dinner. Start with the lobster stuffed avocado served with chipotle mayo, roasted corn, salsa, and tortilla chips. Lobster entree options include creamy lobster mac and cheese, a classic lobster roll, or an Italian-inspired lobster bruschetta. Mile Marker One is all local, all lobster, all the time — yum!
Located in the heart of the marina and offering gorgeous views, Mile Marker One is a prime spot for soaking up the Gloucester coastal vibe.
Pro Tip: While Wingaersheek Beach has a concession stand for a quick lunch, explore your options for a delicious dinner dining experience. Be sure to make reservations to avoid a lengthy wait for a table.
Stunning Beach House Destinations
Ocean View Retreat
Evensong is a lovely ocean view retreat with views of the Annisquam River and Wingaersheek Beach. Offering beautiful vistas and water access for kayakers or paddle boarders (bring your own), colorful sunsets, and waterfowl sightings, you will love this relaxing vacation getaway stay. With three bedrooms and two baths, the rental sleeps six and is roomy enough for a small family gathering and cozy enough for a romantic getaway.
Classic Beach Cottage
If you desire a getaway with ocean views at your doorstep, this classic beach cottage may be the perfect spot. This quaint beachy rental is located on the Annisquam River — at high tide, the water rises under the deck. Offering access to Wingaersheek Beach, Annisquam Village, and a private beach, drop your bags and sink into your on-the-beach, tranquil escape. Image sipping your favorite beverage while watching the tide flow right up to you. It doesn’t get any better than that.
Local Rental Agency
Annisquam Village Realty has a nice selection of area vacation rentals. Booking a stay with a trusted local agency gives you confidence that your getaway stay will be exactly as promised.
Pro Tip: Booking a stay within walking distance to Wingaersheek Beach will enhance your Gloucester getaway with ocean views and proximity to all the beachy 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 under an hour to get to the center of Gloucester when traffic is light — longer on Fridays during the summer.
Road trippers will love the ride from Boston to Glouester. You can make the trip in under an hour or take your time and explore along the route.
If you don’t want to drive, the train from North Station (this will require a ride share or 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. Plan for extra driving time during peak weekend getaway hours.
Elegant Gloucester Beach Getaway
When you are planning your upcoming ocean getaway, add Gloucester’s Wingaersheek Beach to your sun-filled beach bucket list. This charming Massachusetts north shore locale is a beautiful vacation destination. Gloucester is the perfect spot to experience the freshest seafood, explore the unique coastline, and fall in love with Wingaersheek Beach.
Explore everything else Massachusetts has to offer, including:
