Winchester, MA Road Trips
Plan drives from Winchester, MA with practical route pages for distance, drive time, fuel cost, road character, and places to stop along the way.
Photo: Wikimedia Commons
Trip Routes
1
Longest Drive
59.5 mi
Fall River, MA
Quickest Drive
1h 17m
Fall River, MA
Plan Around Winchester, MA
Popular Incoming Routes
Useful if Winchester, MA is the arrival point and you want the strongest routes into the city first.
Winchester, MA by the Numbers
Recent demographic snapshot from the US Census Bureau's American Community Survey.
Population
22,862
Median Income
$218,176
Median Home Value
$1,181,700
Median Age
43.0
Source: US Census Bureau ACS 5-year (public domain). See our methodology for details.
Winchester, MA at a Glance
Founded
1640
Elevation
62 ft
Area
2 mi²
Sister Cities
Notable People from Winchester, MA
A sampling of people born in Winchester, MA.
Mark A. Milley
1958
American military personnel (born 1958)
Brad Whitford
1952
American guitarist (born 1952)
Maribel Vinson
1911–1961
figure skater (1911-1961)
Richard Phillips
1955
former captain of the MV Maersk Alabama
Jon Favreau
1981
American political pundit (1981-)
Vic Firth
1930–2015
American musician (1930–2015)
Leon Tuck
1891–1953
American ice hockey player (1891–1953)
Lyman Bradford Smith
1904–1997
U.S. botanist (1904-1997)
Gordon Smith
1908–1999
American ice hockey player (1908–1999)
Landmarks & Historic Sites
Attractions and heritage-registered places located in Winchester, MA.
Mystic Valley Parkway
Historic road in Massachusetts
St. Mary's Catholic Church
church building in Massachusetts, United States of America
Alfred Vinton House
historic house in Winchester, Massachusetts
Everett Avenue–Sheffield Road Historic District
historic district in Massachusetts, United States
Firth-Glengarry Historic District
historic district in Massachusetts, United States
Wildwood Cemetery
cemetery in Winchester, Massachusetts
Winchester Savings Bank
bank building in Massachusetts, United States of America
Winchester Town Hall
listed on the US National Register of Historic Places
City data from Wikidata (Q991443), available under CC0. Photos from Wikimedia Commons under their respective licenses. See our methodology for details.
Traveler Guide to Winchester, MA
Woburn is a city in the Greater Boston region of Massachusetts with a population of 41,000 (2020). If you want to sound like a local, pronounce it "WOO-burn". Burlington is a town with a population of 26,000 (2020). Home of the Burlington Mall and other retail development. Just south of Woburn, Winchester is a town in the Commonwealth with a population of 23,000 (2020).
1 Woburn Bowladrome, 32 Montvale Ave (Downtown Woburn, Between Montavle Ave and the Walnut Street Parking lot.). Temporarily Closed (As of June 2024) (updated Jun 2024) 2 O'Brien Ice Hockey Rink, 55 Locust St (Woburn, next to and shares parking lot with Joyce Middle School and adjacent soccer fields), ☏ +1 781 938 1620. The O'Brien Ice Rink is an ice rink used for hockey by the Woburn Tanners and Mass Bay Warriors. It is also open for public skating in the winter. (updated Jun 2024)
1 Boston Marriott Burlington, One Mall Road (Burlington), ☏ +1 781-229-6565. 419 rooms equipped with high-speed internet access. (updated Nov 2022) 2 Spark by Hilton Woburn Boston, 14 Hill St (Woburn), ☏ +1 781 933-5363. (updated Sep 2018) 3 Sonesta Select Boston Woburn Burlington, 240 Mishawum Road (Woburn), ☏ +1 781 932-3200, fax: +1 781 935-6163. (updated Sep 2018) 4 Fairfield Inn Boston Woburn, 285 Mishawum Road (Woburn), ☏ +1 781 938-7575, fax: +1 781 937-0623. (updated Sep 2018) 5 Crowne Plaza Boston - Woburn, 15 Middlesex Canal Park Road (Woburn), ☏ +1 781 935-8760. (updated Sep 2018) 6 Hyatt House Boston/Burlington, 2 Van De Graaff Drive (Burlington), ☏ +1 781-270-0800. In an office park. Outdoor pool with Jacuzzi, sports court, fitness center, barbecue pavilion and 24-hour on-site convenience store. Meeting facilities, complimentary hot and cold breakfast buffets daily and social hours Monday through Thursday. Complimentary high-speed Internet access, newspapers and grocery shopping service, wake-up calls upon request. Same-day dry cleaning service, free parking. Pre-arranged shuttle service within a five-mile radius of the hotel is available. (updated Nov 2022) 7 Residence Inn Boston Woburn, 300 Presidential Way (Woburn), ☏ +1 781 376-4000. Studio suites with fully equipped kitchen, living and sleeping area. Complimentary hot breakfast buffet. Monday-Thursday evening hospitality hour in the gatehouse. Indoor swimming pool, heated spa, exercise room.
Woburn is at the intersection of Route 128 and I-93, allowing for easy access to locations throughout Greater Boston. Winchester can be accessed by Route 3 or I-93. Exits 33 and 34 are the closest to Winchester, and 35 and 36 for Woburn. Route 3, 128, and I-95 expressways have exits to Burlington. 1 Anderson Regional Transportation Center, 100 Atlantic Avenue, Woburn. (updated Oct 2023) 2 Wedgemere station, 25 Mystic Valley Pkwy, Winchester. (updated Oct 2023) Amtrak, ☏ +1 215-856-7924, toll-free: +1-800-872-7245. Operates train service around the United States of America. (updated Mar 2022) Route stopping at Anderson Regional Transportation Center : Downeaster operating five or six trains in each direction daily between Brunswick and Boston with stops Freeport, Portland, Old Orchard Beach (seasonal), Saco, Wells, Dover, Durham, Exeter, Haverhill, and Woburn. MBTA Lowell commuter rail line has stops at Anderson Regional Transportation Center and Wedgemere station. MBTA buses include the 350 from Alewife and 134 from Wellington are your best bet, if it shows up, they can be extremely infrequent at times outside of weekdays. The 354 is a rush hour only express bus, so it's not much use. Lexington and Lowell have bus service to the Burlington Mall. Massport Operates Logan Express buses to and from Boston Logan International Airport from Anderson Regional Transportation Center.
Generally the best way, with infrequent MBTA service. The highway and roads that lead to it can get quite congested at rush hour. Outside of rush hour, you will be generally fine traffic wise, but it's not a guarantee. Route 38 and Route 3 travel throughout town. MBTA bus service is generally infrequent in the area, and service is entirely radial towards downtown Boston. There is no overlap in the 134 and 350 bus routes. On weekends service is extremely infrequent or nonexistent.
Travel tips adapted from Woburn (Massachusetts) on Wikivoyage, licensed CC BY-SA 4.0. Content summarized; visit the source for the full article. See our methodology for how we use it.
Trips to Winchester, MA
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