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Every stop worth the detour.
The crowd-favorite places that make a drive worth remembering — waterfalls, beaches, hot springs, hikes, scenic landmarks, dining, breweries, ballparks and more. Browse by category or state, find what's near you, and plan the detour with Roamward.
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121 stopsMA
Sources: 121 Roamward guides · live place map
CyclingCape Cod Rail TrailMA · Rail-traila flat 25-mile cruise through the heart of the CapeView guide →Ski & snowboardBerkshire EastMA · All-mountaina surprisingly steep western-Massachusetts localView guide →MLB ballparksFenway ParkMA · Classicthe oldest park in the majors — the Green Monster, the lone red seat, a hand-operated scoreboardView guide →Wild landsCape Cod National SeashoreMA · National SeashoreForty miles of protected Atlantic dune coastView guide →LighthousesGay Head LightMA · Atlantic Coastatop the colorful clay cliffs of Martha’s VineyardView guide →WaterfallsBash Bish FallsMA · Short walkthe tallest single-drop fall in Massachusetts, split by a boulderView guide →LighthousesHighland (Cape Cod) LightMA · Atlantic CoastCape Cod’s oldest and tallest light, moved back from an eroding cliff in 1996View guide →LighthousesNauset LightMA · Atlantic Coastthe red-and-white tower from the Cape Cod potato-chip bagView guide →HikesBash Bish FallsMA · Easythe tallest single-drop falls in the stateView guide →LighthousesNobska LightMA · Atlantic Coasta classic cast-iron light over Vineyard Sound at the elbow of Cape CodView guide →Ski & snowboardJiminy PeakMA · Familythe Berkshires’ biggest, family-friendly with night skiingView guide →BeachesChatham Lighthouse BeachMA · Scenicshifting outer-Cape sandbars below the lighthouse and seal-rich Atlantic waterView guide →BeachesCoast Guard BeachMA · Scenica wild, dune-backed Cape Cod National Seashore beachView guide →BeachesCrane BeachMA · Familyfour miles of soft sand and dunes north of BostonView guide →HikesBlue Hills (Skyline Loop)MA · Moderaterocky ridgeline views over BostonView guide →GolfBoston Golf ClubMA · privateOne of Hanse's early original designs, a wild, rough-edged course south of Boston that helped establish his minimalist reputation.View guide →WaterfallsDoane’s FallsMA · Short walka series of cascades through a hemlock gorgeView guide →Ski & snowboardWachusett MountainMA · Familya central-Mass learning hill close to BostonView guide →BeachesGood Harbor BeachMA · Familya wide, scenic Cape Ann beach with a tidal island to exploreView guide →DiningAlden & HarlowMA · New AmericanSubterranean Harvard Square hit for inventive shared plates.View guide →Breweries & distilleriesHarpoon BreweryMA · Brewerya Seaport beer hall with fresh pretzels and harbor viewsView guide →BeachesHorseneck BeachMA · Familya long Buzzards Bay beach with dunes, warm water, and campground accessView guide →Breweries & distilleriesJack’s Abby Craft LagersMA · Breweryall-lager brewing in a huge, lively beer hall west of BostonView guide →BeachesKatama BeachMA · ScenicMartha’s Vineyard south-shore sand with open ocean surf and big skyView guide →GolfCrumpin-FoxMA · publicA scenic Roger Rulewich course in the western hills.View guide →GolfCyprian KeyesMA · publicA rolling public course in central Mass.View guide →BeachesMarconi BeachMA · Scenictall Cape Cod bluffs, big Atlantic surf, and national seashore dramaView guide →BeachesMayflower BeachMA · Familya Cape Cod Bay beach with tidal flats, warm shallows, and sunset colorView guide →Breweries & distilleriesNight Shift BrewingMA · Brewerya creative, community-minded brewery just north of BostonView guide →Breweries & distilleriesNotch BrewingMA · Brewerysession beers and a Czech-style biergarten on the Salem waterfrontView guide →BeachesNahant BeachMA · Scenica long tombolo beach with Boston skyline glimpses and rocky North Shore edgesView guide →BeachesNauset BeachMA · Surfa long, dune-backed outer-Cape beach with real surfView guide →GolfEssex County ClubMA · privateOne of Ross's earliest American projects and a club where he served as professional, making it foundational to his career. A seaside New England classic.View guide →DiningAsmaraMA · EthiopianLongtime Central Square spot for communal Eritrean-Ethiopian platters.View guide →Breweries & distilleriesSamuel Adams BreweryMA · Brewerythe Jamaica Plain birthplace of the beer that sparked America’s craft revivalView guide →GolfGeorge WrightMA · publicA Donald Ross municipal masterpiece in Hyde Park.View guide →HikesHalibut PointMA · Easya granite-quarry coast walk on Cape AnnView guide →DiningB&G OystersMA · SeafoodBarbara Lynch's intimate South End oyster bar exploring classic New England seafood with a raw bar and seasonal menu. Order: Raw oysters.View guide →GolfGranite LinksMA · public27 holes on reclaimed land with Boston skyline views.View guide →BeachesRace Point BeachMA · Wildthe wild outer tip of Cape Cod, great for whales and sealsView guide →BeachesRevere BeachMA · FamilyAmerica’s first public beach, a broad transit-accessible crescent just north of BostonView guide →DiningBakedMA · Bakery & PieSmall-batch bakery and cafe in Shelburne Falls, a sweet Mohawk Trail pause near the Bridge of Flowers.View guide →BeachesSalisbury BeachMA · Familya Merrimack River mouth beach with broad sand and north-shore summer energyView guide →WaterfallsRoyalston FallsMA · Moderate hikea slot-gorge plunge in north-central MassachusettsView guide →Breweries & distilleriesTree House BrewingMA · Brewerya cult New England IPA destination with a stunning country campusView guide →Breweries & distilleriesTrillium BrewingMA · Brewerya Boston favorite famous for hazy IPAs and a Fort Point beer gardenView guide →DiningBarrington Brewery & RestaurantMA · BrewpubRustic solar-powered brewpub pouring its own barn-brewed beer alongside scratch-made comfort food in the Berkshires since 1995. Order: solar-brewed ale and burgView guide →BeachesSinging BeachMA · Scenicsand that "sings" underfoot on the North ShoreView guide →Breweries & distilleriesWormtown BreweryMA · BreweryWorcester’s hometown brewery, home of Be Hoppy IPAView guide →BeachesMadaket BeachMA · ScenicNantucket’s best sunset beach at the island’s western tipView guide →WaterfallsWahconah FallsMA · Short walkan easy Berkshires fall in its own small state parkView guide →DiningBergamotMA · New AmericanRefined Union Square New American with a seasonal menu and lauded wine and cocktail program in an understated space. Order: Handmade pasta.View guide →HikesMonument MountainMA · Moderatea Berkshire quartzite ridgeView guide →HikesMount GreylockMA · Hardthe state high point, with a war-memorial towerView guide →GolfOld SandwichMA · privateA spacious, sand-floored club south of Boston where firm turf and generous corridors invite a creative, ground-game style of play.View guide →HikesMount Tom (Holyoke Range)MA · Moderatetraprock cliffs over the Pioneer ValleyView guide →GolfOlde Scotland LinksMA · publicA links-style municipal south of the city.View guide →HikesMount WataticMA · Moderatea bald summit at the south end of the Wapack RangeView guide →DiningBlue Heron RestaurantMA · New AmericanA Connecticut River valley dinner stop that gives the Mohawk Trail corridor a more polished option near the eastern approach.View guide →DiningBlue RockMA · New AmericanA Shelburne Falls dinner pick that gives the Mohawk Trail a polished stop near the Bridge of Flowers.View guide →
Category guides
Go deeper, interest by interest.
121 stops across 19 state-by-state guide collections.
Hikes500+ trails in every state, easy to epic545 stops →Waterfalls300+ falls, roadside to bucket-list303 stops →BeachesFamily sand, surf breaks, and wild shores299 stops →Hot springsLuxe resorts to wild backcountry soaks90 stops →Mountain bikingTrail systems, bike parks, and gravel76 stops →CyclingScenic rides, climbs, and rail-trails50 stops →Ski & snowboardBig-mountain steeps to family hills86 stops →DiningGreat meals near routes and gateway towns3,924 stops →Breweries & distilleriesTrip-worthy taprooms and still houses267 stops →GolfPublic courses you can actually book753 stops →National parksAll 63, guided by season and top sights63 stops →Hidden gemsVote favorites into the Roamward map19 stops →MLB ballparksAll 30 MLB parks as a road-trip quest30 stops →LighthousesCoast-to-coast beacons worth the drive60 stops →EventsPlan the trip around the moment31 stops →Wild landsForests, wilderness, and monuments beyond the parks74 stops →CampingEpic campgrounds by where you want to wake up63 stops →Scenic landmarksIconic overlooks, canyons, dunes, and formations57 stops →Roadside AmericanaGiant statues, folk art, oddities, and vintage neon23 stops →
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