48 Hours in Mystic, Connecticut: The Ultimate Itinerary

Mystic, CT
Barry Winiker / Getty Images

Think of Mystic, Connecticut, and the first thing that comes to mind may be the 1988 Julia Roberts film “Mystic Pizza” and the eponymous pizzeria it was based on. But this coastal New England town is more than just a slice shop: it’s a maritime getaway with a boatload of American history. Situated on the banks of the Mystic River—the two sides are linked by the famous Mystic River Bascule drawbridge—this village was once a powerhouse of the shipbuilding industry, where more than 600 vessels were constructed. When the shipbuilding boom halted after the Civil War, the town transformed itself into a charming nautical-themed destination that enchants millions of visitors today.

Just a two to three-hour drive from New York City or Boston, Mystic is a perfect weekend city escape for those craving a sophisticated food scene, unique shopping, and plenty of gorgeous views. Planning a trip? Here’s what needs to be on your itinerary.

01 of 06

Day 1: Morning

The Whaler's Inn

Courtesy of The Whaler's Inn

10 a.m.: Check in to The Whaler’s Inn. Located in the heart of downtown, this nautical-themed boutique hotel is a Mystic mainstay. A primary site of hospitality in the town for the past 150 years, the Inn’s 45 guest rooms are housed inside five historic buildings, all of which retain charming historical touches, such as original floors and tin ceilings from 1910. A slew of recent renovations have given the guest rooms a chic and modern feel, and you won’t be able to beat the direct view of the Mystic River Bascule Drawbridge from Hoxie House.

11 a.m.: Though it’s small in size, Mystic boasts a bustling downtown filled with shops, restaurants, galleries, and more. There’s no better way to get situated than to take a stroll and explore. Grab a scoop of homemade ice cream at Mystic Drawbridge Ice Cream, then check out the unique offerings at crafts shop Mystic Knotwork, where you can find handmade nautical knot bracelets, coasters, ornaments, doormats, and more. Next, head to Peppergrass & Tulip, a great place to sift through vintage clothing and Victorian-era inspired gifts, and pop into local favorite Bank Street Books, where you can shop your favorite paperbacks from a small, local business. Other great options for gifts include Hang the Moon, Trove, Main Street Soap Emporium, and Mystic Disc, a hidden gem for vinyl diehards. 

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02 of 06

Day 1: Afternoon

Grass & Bone

Courtesy of Grass & Bone

1 p.m.: A short walking distance from The Whaler’s Inn, head to lunch at Grass & Bone. This hybrid butcher shop-restaurant redefines “farm to table.” Diners are drawn toward the front counter, where a display of freshly butchered meat can be found alongside the names of the local farms they were raised on. Meat isn’t the only thing locally sourced: the restaurant sources its dairy products from Lebanon, Connecticut’s Mystic Cheese Company, and its bread from Haddam, Connecticut’s Farm to Hearth bakery. Some of their most popular dishes include the Autumn Rotisserie chicken sandwich, made with free-range chicken from Free Bird farm in Lebanon, Pennsylvania, and their delicious cornbread with maple butter, made with cornmeal from Davis Farm in Pawcatuck, Connecticut. As you head out, you can purchase a cut of meat from the front counter for a future meal.

3 p.m.: One of the most esteemed maritime museums in the United States, the Mystic Seaport Museum is an essential stop on your weekend trip. As steamships and railroads gained more popularity after the Civil War and the grand wooden vessels that Mystic was known for building began to disappear, this museum was created as an educational institution to preserve the country’s maritime culture. Today, the museum features everything from a working shipyard and a recreated 19th-century seafaring village. The crown jewel is the Charles W. Morgan, the world’s last wooden whaleship. Tickets are $19 for adults and $16 for children; if you’re planning to visit the Mystic Aquarium next door, purchase a Mystic Pass for discounted access to both attractions.

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03 of 06

Day 1: Evening

The Shipwright's Daughter

Courtesy of The Shipwright's Daughter

7 p.m.: One of the perks of staying at The Whaler’s Inn is easy access to their buzzy on-site restaurant, The Shipwright’s Daughter. One of Mystic’s newest culinary additions, the daily-changing, coastal-inspired menu prioritizes sustainability by using all parts of its locally sourced fish to create its many flavorful dishes. Start with oysters and explore the unique cocktail menu, featuring drinks such as The Pharmacist, made with Old Forester Bourbon, yellow chartreuse, chamomile, and sage. Don’t miss dishes like the Stonington scallops, with heirloom carrots, pickled persimmon, and ginger chive, and the pan-roasted pork chop with stuffed baby sweet potatoes, mushroom, almond, smoked beet, and chipotle maple glaze. End your meal with an espresso martini, one of the restaurant’s specialties, then stroll the few steps back to your hotel room.

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04 of 06

Day 2: Morning

Sift Bake Shop

Courtesy of Sift

10 a.m.: Breakfast courtesy of The Shipwright’s Daughter is included in your stay at The Whaler’s Inn—and you should definitely take advantage of their biscuits. But if you’re craving a treat, head over to Sift Bake Shop, an artisanal bakery that draws a devoted crowd upon its opening every morning. Grab a scone or sticky bun, or try a unique savory pastry, like the vegetable croissant featuring spinach, sun-dried tomatoes, garlic, feta, Parmesan, and white sesame seeds. Sift’s menu also features decadent delights such as macarons, tarts, and an excellent mille-feuille. Still, you’d be remiss not to order a loaf of their freshly made bread, which is baked in-house every morning beginning at 3 a.m.

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05 of 06

Day 2: Afternoon

Tourists wandering around at Olde Mistick Village in Mystic of Connecticut
aimintang / Getty Images

1 p.m.: It’s time for the moment that was probably at the top of your list: a fresh slice at the world-famous Mystic Pizza. Opened in 1973 by the Zelepos family, this pizzeria was a locals’ favorite long before it found Hollywood success. How exactly did its claim to fame come about? Legend has it that screenwriter Amy Jones, who was vacationing in Mystic, popped into the pizzeria one summer and was immediately inspired to write a coming of age story about three young pizza waitresses in a small fishing village. The eponymous film, which starred Julia Roberts and was the screen debut of actor Matt Damon, was a big hit upon its release in 1988. Although its interior scenes were not filmed inside the actual Mystic Pizza, it inspired a wave of tourists who continue to flock to the town to experience the same magic from the movie. Order by the slice or grab a pie for takeout—and don’t forget to snap a photo with the bright blue storefront sign, which was renovated to resemble the exterior in the film.

3 p.m.: For a true taste of colonial New England, head to Olde Mistick Village, a part of town distinctly designed to represent the old architecture of the 1720s. Complete with a duck pond, birdhouses, and a gazebo, the area is truly picturesque and historic down to the last detail: no two buildings look the same. While you take in some great scenery, you can also enjoy Olde Mistick’s top-notch shopping and dining. Grab a donut from artisanal donut shop Deviant Donuts, then pop into Franklin’s General Store, featuring New England treats like saltwater taffy and local jams, and Toy Soldier, an independent, family-owned toy shop that is sure to delight young children.

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06 of 06

Day 2: Evening

Open Drawbridge
AlbertPego / Getty Images

6 p.m. In operation since 1920, the Mystic River Bascule Drawbridge is one of the first things you’ll see when you arrive in downtown Mystic. Connecting the two sections of Mystic—Groton and Stonington, one of the most magical experiences you can have on your trip is to experience the drawbridge's raising as it allows boat traffic to pass through. This happens every 40 minutes past the hour from 7:40 a.m. to 6:40 a.m. May 1 to Oct. 31, and on-demand all other times. An incredible place to take in this view is at S&P Oyster Restaurant & Bar, situated right next to the drawbridge and featuring an outdoor space complete with individual fireplaces at every table for colder months. Order a cocktail and kick back—this is truly an authentic New England experience. 

8 p.m. Your trip to Mystic would not be complete without a reservation at Oyster Club, the crown jewel of Mystic’s sea-to-table dining scene. The restaurant’s ocean blue exterior beckons you to enter and experience its eclectic menu, intertwining Oaxacan influences, locally sourced seafood, and unique fermentation processes into each dish. Nestled high above Oyster Club, you’ll find The Treehouse, the restaurant’s outdoor extension—a literal wooden cabin elevated by a long staircase and surrounded by trees—is one of the most magical dining experiences in New England. Whether you dine outdoors or indoors, you’ll have a hard time finding something on Chef James Wayman’s menu that doesn’t knock it out of the park. Order the Cocktail Number 7, made with mezcal, beets, ginger, fermented fennel, rose shio syrup, and lime, and don’t miss out on the namesake oysters. Your best bet will be to go all-in on the menu’s “Dinner Party Experience,” a four-course prix fixe menu curated by the chef and featuring a welcome cocktail—all for the incredibly reasonable price of $65. It’s the perfect way to celebrate a weekend well done in one of America’s most beautiful towns.