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Winchester, MA Road Trips

Sitting in the Northeast, Winchester, MA is a local road trip base with 6 trip routes mapped and ready to explore. Most drives stay under 9 miles, making this area well-suited for day trips and weekend getaways. Most routes from Winchester, MA head west, giving the route network a clear directional lean.

city and unparished area within the larger City of Winchester, Hampshire, England

Photo: Wikimedia Commons

Trip Routes

6

Longest Drive

65.4 mi

New Bedford, MA

Quickest Drive

15m

Waltham, MA

Plan Around Winchester, MA

Continue From Winchester, MA

Good next legs if this city is only one stop in a longer road trip.

Trips from Winchester, MA

Driving from Winchester, MA

On average, trips departing from Winchester, MA run 9 miles with a drive time of roughly 15m. The majority of routes are short drives — quick enough to finish before lunch and be back for dinner. The longest mapped route runs 9 miles (15m), while the shortest is just 9 miles.

Popular Destinations

The most popular drives from Winchester, MA include Waltham, MA (8.8 mi, 15m). Most destinations stay within the same state, perfect for exploring the local region thoroughly.

Planning & Costs

For the average 9-mile drive from Winchester, MA, expect to burn about 0.4 gallons of fuel one way at 25 MPG. Check local pump prices before you go to lock in your budget.

Most routes head west — leaving in the morning keeps the sun behind you for a more comfortable drive. With an average drive under three hours, you have plenty of flexibility — leave whenever it suits you.

Frequently Asked Questions

There are 1 mapped routes leaving Winchester, MA and 5 routes heading into Winchester, MA, covering 6 total connections. Distances range from 9 to 9 miles.

The longest mapped route from Winchester, MA covers 9 miles and takes approximately 15m. Shorter options start at just 9 miles.

The average route from Winchester, MA runs about 9 miles with a drive time of roughly 15m. This includes both short day trips and longer multi-day drives.

The most popular road trip destinations from Winchester, MA include Waltham, MA. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.

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

Saint-Germain-en-Laye

Notable People from Winchester, MA

A sampling of people born in Winchester, MA.

Mark A. Milley

Mark A. Milley

1958

American military personnel (born 1958)

Brad Whitford

Brad Whitford

1952

American guitarist (born 1952)

Maribel Vinson

Maribel Vinson

1911–1961

figure skater (1911-1961)

Richard Phillips

Richard Phillips

1955

former captain of the MV Maersk Alabama

Jon Favreau

Jon Favreau

1981

American political pundit (1981-)

Vic Firth

Vic Firth

1930–2015

American musician (1930–2015)

Leon Tuck

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

Mystic Valley Parkway

Historic road in Massachusetts

National Register of Historic Places listed place
St. Mary's Catholic Church

St. Mary's Catholic Church

church building in Massachusetts, United States of America

National Register of Historic Places listed place
Alfred Vinton House

Alfred Vinton House

historic house in Winchester, Massachusetts

National Register of Historic Places listed place
Everett Avenue–Sheffield Road Historic District

Everett Avenue–Sheffield Road Historic District

historic district in Massachusetts, United States

National Register of Historic Places listed place
Firth-Glengarry Historic District

Firth-Glengarry Historic District

historic district in Massachusetts, United States

National Register of Historic Places listed place
Wildwood Cemetery

Wildwood Cemetery

cemetery in Winchester, Massachusetts

National Register of Historic Places listed place
Winchester Savings Bank

Winchester Savings Bank

bank building in Massachusetts, United States of America

National Register of Historic Places listed place
Winchester Town Hall

Winchester Town Hall

listed on the US National Register of Historic Places

National Register of Historic Places listed place

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

Nearby Hubs

Other cities within driving distance of Winchester, MA that also have route pages.

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Where to go from Winchester, MA?

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