A weekend escape to Gloucester, on Massachusetts’ other cape- Cape Ann- makes for a picturesque seaside getaway. I love that there is a big variety of outdoor activities to fill the days. You most certainly won’t be bored! Gloucester gets bonus points for having so many great restaurants with lots of fresh seafood.
Where to Stay in Gloucester
When you’re taking a short trip, you want to maximize your time. A hotel with a convenient location and lots of amenities is the way to go. Beauport Hotel in Gloucester checks those boxes. Beauport sits on Pavilion Beach overlooking Gloucester Harbor. The harbor views are beautiful and can be enjoyed through the window of your oceanfront room or on the expansive outdoor deck. The hotel sits just around the corner from downtown, so it’s an easy walk to all the restaurants and shops.
If you prefer views of the open ocean instead of the harbor, opt to stay at the historic Ocean House Hotel or the Atlantis Oceanfront Inn. Both have absolutely gorgeous eastward facing views. Rooms face the ocean so you can sip your morning coffee on the balcony and watch the day unfold as the sun rises. Perfect!
What To Do
Visiting Gloucester and the surrounding towns provides ample opportunity to get out and explore the beautiful surroundings. A few of my favorites:
- Stand Up Paddle Boarding– If you’re staying at the Beauport you can conveniently walk out the door to Pavilion Beach and find Cape Ann SUP. They’re one of the best SUP outfitters and tour operators in the area so you definitely have to give SUP a try if you never have. They offer lessons, and more experienced paddlers will enjoy their tours around Gloucester Harbor or on the picturesque Essex River.
- Sea Kayaking– Another awesome way to explore the coast is by kayak and there are several spots to try. Take a sunset kayak tour of the Crane Wildlife Refuge or paddle the Rockport coast with a rental or tour from North Shore Kayak Outdoor Center.
- Road Cycling– Cape Ann is one of my favorite places to ride. From Manchester up through Rockport, there are some great roads winding along the water. Riding along Gloucester’s eastern shore and north to Rockport is a great route. I have a couple routes mapped out on Ride with GPS that start in Ipswich and head out to Rockport. Contact me if you would like a custom route designed just for you.
- Mountain Biking– While you won’t find any mountains at sea level, there are quite a few mountain biking trails in the area. Willowdale State Forest in Ipswich and Topsfield is one of the most popular. There’s a huge network of trails in Willowdale, and it’s easy to get lost, so be sure to bring a map or use a GPS. For those looking for a few easier trails, head to Gordon College in Wenham to explore the rolling double track in Chebacco Woods.
- Trail Walks– There are tons of trails to walk in and around Gloucester. Whether you want to walk along the water, through sand dunes or in the forest, there is a trail for you. I love walking the dunes trails at Crane Beach in Ipswich. It’s a great workout and the scenery is amazing. For a quieter stroll, walk along Stacey Boulevard boardwalk in Gloucester, or head to Rockport where there is a little known public foot path that runs along the ocean in front of the Emerson Inn. The name is Atlantic Path, and it runs all the way to Halibut Point Park. The views are gorgeous! The Trustees of Reservations manages a great property for meandering the woods in Gloucester- Ravenswood Park. I recommend heading out on the orange Ledge Hill Trail and making a loop by coming back down the Old Salem Road.
- Beaches– Sometimes you just need a little down time. A few hours on a beach is good for the soul. Good Harbor and Wingaersheek Beaches in Gloucester are the city’s largest and most popular beaches. For smaller beaches within walking distance to shops and restaurants, head to Rockport, where you’ll find Front, Back and Old Garden Beach.
Stacey Boulevard, Gloucester 
Atlantic Path, Rockport
Where To Eat
- 1606 Restaurant– This is located in the Beauport Hotel, and it’s a wonderful spot to enjoy fresh seafood and overlook the harbor. The large bar has waterfront views and opens to the outdoor dining deck. On cooler days there is a large fire pit on the deck to keep you warm as you sip your favorite drink. Be sure to order a few local oysters- one of my favorite superfoods.
- Minglewood Harborside– Within walking distance of the Beauport is this popular spot tucked into the working harbor. I recommend ordering off the extensive sushi menu. Go for lunch or early dinner and you might see a fishing boat unloading its daily catch. I’ve seen some pretty big tuna lifted off those boats.
- Tonno– Definitely one of my favorites! It’s a cozy Italian seafood spot with amazing food. Definitely order the stewed clams with white beans and pancetta. You’ll thank me later.
- Willow Rest– I love a good lunch counter, and Willow Rest has one. This long time spot is popular with the locals and features a market with a quick serve breakfast and lunch menu. Enjoy your meal at the counter, on one of the picnic tables or take it to go.
- The Last Stop– Be careful, or you’ll drive past this little gem. It’s on East Main Street, heading to East Gloucester and is the perfect spot for a quick morning bite or mid-day lunch. They have all the basics covered- eggs, salads, smoothies and fresh sandwiches on locally baked bread.
- Lobster Pool– You can’t have a list of restaurants in the Gloucester area without including a place to eat Lobster. Splendid ocean views and all the ocean fresh seafood you could want. Not much more to say.
- Brothers Brew Coffee Shop– Stroll downtown Rockport and nearby Bearskin Neck with a brew in hand from Brothers. I love their coffee and it’s a good spot for a quick lunch or breakfast. Yes, they might have the best donuts around but you didn’t hear that from me.
- Castaways Vintage Cafe– This super cute and funky cafe offering coffee, smoothies and açaí bowls has a Main Street address but the cafe entrance is on Rogers Street. While you’re there check out their eco-friendly, recycled clothing in the shop upstairs.
I hope I’ve given you enough ideas to start planning your weekend (or perhaps week long) trip to Gloucester. Feel free to leave a comment if there is something else you’re looking to do.