Begin your journey with a unique potato donut from [The Holy Donut](https://www.theholydonut.com) before diving into local history with a quiet walk through the ancient, weathered gravestones of Eastern Cemetery. Conclude your morning navigation through the charming, fog-laden cobblestone alleys of the Old Port, where the city's maritime past and 19th-century architecture set a perfectly moody New England tone.
Satisfy your hunger with a visit to [Highroller Lobster Co.](https://www.highrollerlobster.com) for a modern twist on the classic roll before exploring the bizarre and fascinating exhibits at the [International Cryptozoology Museum](https://www.cryptozoologymuseum.com). Afterward, walk over to [Bissell Brothers Brewing Company](https://www.bissellbrothers.com) to sample their legendary IPAs in a vibrant, industrial setting that perfectly captures Portland's craft culture.
As the winter sun sets over the harbor, enjoy a hearty dinner of poutine and Panini at [Duckfat](https://www.duckfat.com) before descending into the subterranean, candlelit warmth of [Bramhall](https://www.bramhallme.com) for craft cocktails in a historic basement setting. Finish your night with a walk past the darkened facade of the Wadsworth-Longfellow House, where the shadows of the 18th-century structure provide a perfect introduction to the spooky history of New England.
Depart Portland for a scenic drive south, arriving in Salem just in time to enjoy a bohemian breakfast at the quirky [Gulu-Gulu Cafe](https://www.gulugulucafe.com). Afterward, take a crisp winter stroll across the historic Salem Common to admire the surrounding Federal-style architecture before paying your respects at The Burying Point, the city's oldest cemetery, where colonial-era headstones lean at haunting angles against the cold January sky.
Head to [The House of the Seven Gables](https://7gables.org) to explore the mysterious secret staircases of the historic 1668 mansion before warming up with a flight of session ales at the riverside [Notch Brewing](https://www.notchbrewing.com). Afterward, browse the macabre curiosities at [The Witchery](https://www.thewitcherysalem.com), where you can craft your own ritual broomstick or explore a curated collection of occult wonders.
After a delicious dinner of fresh New England fare at [Finz Seafood & Grill](https://www.google.com/search?q=Finz+Seafood+%26+Grill+Trip+to+Portland+Maine+%281+night%29+Salem+mass+%282+nights%2C+Boston+%282+nights%29+%0A%0AWe+like+food%2C+breweries%2C+spooky+activities++official+site), join the [Salem Night Tour](https://www.salemghosttours.com) to wander through the shadows of the city's most haunted sites as lanterns flicker in the winter wind. Conclude your evening by warming up with a unique, experimental draft at [Far From The Tree Cider](https://www.farfromthetreecider.com), reflecting on the eerie histories shared by your guide.
Immerse yourself in the dark history of 1692 at the [Salem Witch Museum](https://www.salemwitchmuseum.com), where dramatic presentations recreate the hysteria and trials that defined the city's past. Afterward, take a somber walk to the nearby Salem Witch Trials Memorial to pay your respects at the cantilevered stone benches before capturing a photo of the iconic Old Town Hall, the historic site of the city's original municipal markets.
Enjoy a quirky lunch at [The Flying Saucer Pizza Company](https://www.flyingsaucerpizzacompany.com) before stepping into the [The Witch House](https://www.thewitchhouse.org), the preserved 17th-century home of Judge Jonathan Corwin and the only structure in Salem with direct ties to the trials. Afterward, immerse yourself in the world of cinematic horror and macabre history at [Count Orlok's Nightmare Gallery](https://www.nightmaregallery.com), providing a thrilling bridge to your evening of spirits and spirits.
Cap off your night by joining the [Boos and Brews Haunted Pub Crawl](https://www.google.com/search?q=Boos+and+Brews+Haunted+Pub+Crawl+Trip+to+Portland+Maine+%281+night%29+Salem+mass+%282+nights%2C+Boston+%282+nights%29+%0A%0AWe+like+food%2C+breweries%2C+spooky+activities++official+site), where you will hear chilling ghost stories while stopping for local spirits at some of the city's most storied taverns. Before the tour, enjoy a hearty dinner at [Village Tavern](https://www.villagetavernsalem.com), then head to [East Regiment Beer Co.](https://www.eastregimentbeerco.com) to sample small-batch brews in an atmosphere that honors the town's colonial militia history.
Bid farewell to Salem and arrive in Boston for a hearty breakfast at [The Paramount](https://www.paramountboston.com) on the iconic, gas-lit streets of Beacon Hill. Afterward, start your journey along the Freedom Trail, pausing to explore the ancient, weathered headstones of Revolutionary icons at the Granary Burying Ground and the chilling, centuries-old carvings at King's Chapel Burying Ground.
Continue your historical trek toward the North End to walk among the weathered headstones of Copp's Hill Burying Ground, a site famously once used as a British battery during the Battle of Bunker Hill. Afterward, warm up with a flight of local craft beers at [Night Shift Brewing - Lovejoy Wharf](https://www.nightshiftbrewing.com) before heading to the historic [Union Oyster House](https://www.google.com/search?q=Union+Oyster+House+Trip+to+Portland+Maine+%281+night%29+Salem+mass+%282+nights%2C+Boston+%282+nights%29+%0A%0AWe+like+food%2C+breweries%2C+spooky+activities++official+site) for a sampling of freshly shucked oysters and their legendary clam chowder in the nation's oldest continuously operating restaurant.
Spend your evening at the [Bell in Hand Tavern](https://www.google.com/search?q=Bell+in+Hand+Tavern+Trip+to+Portland+Maine+%281+night%29+Salem+mass+%282+nights%2C+Boston+%282+nights%29+%0A%0AWe+like+food%2C+breweries%2C+spooky+activities++official+site), where you can enjoy a hearty meal in a space that has held the first booze license in the United States since 1795. Afterward, venture into the shadow-drenched corridors of the Omni Parker House to hear tales of its resident spirits before concluding the night with a draft beer at the [21st Amendment](https://www.google.com/search?q=21st+Amendment+Trip+to+Portland+Maine+%281+night%29+Salem+mass+%282+nights%2C+Boston+%282+nights%29+%0A%0AWe+like+food%2C+breweries%2C+spooky+activities++official+site), a cozy pub tucked away in a 19th-century building near the State House.
Kick off your final day with a cozy breakfast of handmade Italian treats at [Modern Pastry](https://www.modernpastry.com) before exploring the somber history of the Central Burying Ground, one of the city's most haunted and overlooked cemeteries. Afterward, head to the waterfront to meet your doom-obsessed guide for the [Ghosts & Gravestones Tour](https://www.ghostsandgravestones.com/boston), where you'll hear chilling tales of the Boston Strangler and the city's more macabre residents while traversing the cobblestone streets one last time.
Savor the flavors of the North End by grabbing a legendary Italian sub from [Monica's Mercato](https://www.google.com/search?q=Monica%27s+Mercato+Trip+to+Portland+Maine+%281+night%29+Salem+mass+%282+nights%2C+Boston+%282+nights%29+%0A%0AWe+like+food%2C+breweries%2C+spooky+activities++official+site) before exploring the chilling history of the crypt underneath the Old North Church. Afterward, transition from the historical to the modern with a short trip to the Fort Point district to sample world-renowned craft beers at [Trillium Brewing Company](https://www.trilliumbrewing.com), reflecting on your journey through New England's most spirited cities.
Conclude your New England adventure with an intimate candlelit dinner of Sicilian seafood at [The Daily Catch](https://thedailycatch.com) before heading to The Liberty Hotel to explore the site of the former Charles Street Jail. Sip a final craft cocktail at [Alibi](https://www.alibiboston.com), where the bar is set directly within the old granite prison cells, providing a perfectly atmospheric and historical end to your spooky journey.