How to Plan a Winter Staycation in Salem, MA

Stay local and explore our historic seaport with a Salem staycation! Relax with an overnight stay within walking distance to shops and restaurants, and visit favorite museums and attractions, take in outdoor public art around town, and more. Find ideas to plan your stay below, and read to the end of this post to learn how you could win a Salem staycation featuring many of the recommendations included here.

Day 1

Start your staycation off with something sweet for breakfast at Caramel Patisserie. With croissants, macarons, tartes, and baguettes, plus caffeine in the form of espressos and cappuccinos you’re sure to find something to satisfy your sweet tooth while you prepare to head out for your first day of exploring Salem.

Stroll down Essex Street and take in the newest holiday decorations in place downtown, including the Christmas tree in Lappin Park and the newly lit light polls adorned with wreaths and ribbons. While on the pedestrian mall, pick up your next read at Wicked Good Books, Salem’s independent book store, or make a quick detour onto Central Street to discover new clothing and accessories at Modern Millie and Emporium 32. Back on Essex Street, Pamplemousse has kitchen gadgets and gourmet gifts that are sure to be perfect for someone on your list along with a nice selection of local craft beer and wine to bring back to your hotel.

Wicked Good Books

Visit the Peabody Essex Museum to explore Salem’s art and culture along with works brought back to Salem by merchants who traveled around the world, and take in the museum’s latest exhibits, The Salem Witch Trials 1692 and Made It: The Women Who Revolutionized Fashion. (The museum is free for Salem residents, just be sure to purchase timed tickets ahead of your visit on pem.org to ensure your space under current capacity limitations.)

Take a right out of the museum and continue down Essex Street to shop the new location for Moody’s Home & Gifts. Their expanded storefront is full of fair trade and locally made gifts and home decor items, perfect for dressing up a new space or finding just the right gift this holiday season. Locals can also take advantage of curbside pickup to shop on the go as the holidays approach.

Moody’s Home & Gifts

For dinner, head towards Washington Street and pickup takeout for dinner at Ledger. Ledger’s menu offers new twists on classics with all of the freshest ingredients, and we recommend following their social media pages to stay up to date with their latest takeout and brunch specials.

While back at home or at your Salem hotel, celebrate the holiday season with some of Christmas in Salem‘s virtual house tours. This annual event has gone virtual for 2020, allowing you to take a look at historic homes professionally decorated for the holidays from wherever you may be. Tours run online through December 31, and tickets and complete information may be found at christmasinsalem.org.

Ledger

Day 2

Start the following morning with breakfast at your hotel, maybe something savory by the fireplace in the Tavern at the Hawthorne Hotel. Or start your day on the go with a grab-and-go breakfast from the Hampton Inn.

Within walking distance from both hotels, you’ll find Punto Urban Art Museum, a large scale open air museum covering Salem’s Point neighborhood with over 85 murals created by artists from all over the world. Grab a map on this page before heading out to explore the murals and be sure to visit puntourbanartmuseum.org for more information about the murals and the artists behind them as you view them.

Harbor Sweets

As you walk back toward downtown, take a quick detour to Harbor Sweets. See chocolates being made on site and purchase something sweet to enjoy later in the day or to gift to someone special during the holidays. While in the store, be sure to pick up some of their specialty hot cocoa- a perfect way to remember your Salem staycation on cooler days this winter.

Once downtown, a stroll through Front Street and Central Street to do some shopping. J. Mode on Front Street offers contemporary styles by brands like Nicole Miller, Tracy Reese, Three Dots, Bailey 44 and more, while over on Central Street Modern Millie specializes in vintage inspired clothing with dresses, separates, and accessories, plus a selection of consignment pieces.

Modern Millie

Grab lunch to do or dine downtown before heading home at Village Tavern. Perfect for appetizers and drinks or burgers and clam chowder, Village Tavern is centrally located to downtown shops and attractions with a menu sure to please the whole family.

Enter to win a Salem staycation! Bring your Stay Local Salem postcard when you shop and dine downtown this month to earn a punch with each purchase made at a participating business. Get five punches, and you’ll be entered to win a Salem staycation! Need a postcard? They’ve been mailed out to Salem residents, and if you’re not from Salem or need an extra postcard you can pick one up from a participating business or email your mailing address to info@salem.org and we’ll send one to you.

Prizes include: Overnight stays at the Hampton Inn or Hawthorne Hotel, gift cards for Caramel PatisserieJ.ModeLedgerMoody’s Home & Gifts, and Village Tavern, plus a couple’s massage by Freedom Massage, 15 minute readings by Hermetic Arts, and two gift checks from the Salem Chamber of Commerce.