Overview
Ashland is a town of 18,000 in Massachusetts approximately 25 miles west of Boston. Ashland was the original starting point of the Boston Marathon and birthplace of the electric clock.
Holliston is a town with a population of 15,000 (2020).
Hopkinton is a town with a population of 19,000 (2020). It is notable as the current starting place of the Boston Marathon.
Sherborn is a town with a population of 4,000 (2020).
4 things to do · 6 places to eat · 2 bars & cafés · 1 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Ashland
Ashland State Park
Rte. 135. Seasonal. 470 acres with swimming, picnicking, boating, fishing, bicycling and hiking. Wheelchair access to the boathouse and by ramp into the pond.
Hopkinton State Park
Bicycling, boating, fishing, hiking, horseback riding, picnicking and cross-country skiing on 1450 acres. Group area that includes a pavilion, playing field, restrooms, picnic tables, and a large grill is available by re…
Lake Winthrop
Tiny Lake Winthrop has several small unstaffed parks and remains open year round. Pleasure Point, just off Winthrop Street features a small beach and a boat launch onto the lake. Stoddard Park features a beach, a gazebo,…
Slot Car Racing at Modelville Hobby
Two 8-lane slot car tracks for 1/32nd and 1/24th scale cars.
Plan your trip
Best time to visit & weather
Most comfortable: May–Sep. Summer highs reach about 80°F; winter lows dip to about 18°F. Cold months (Jan, Feb, Dec) can bring snow and ice; check road conditions. Wettest: Mar and Nov. (climate data from nearby Wellesley)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- BED Laurence G Hanscom Field, Bedford — 17 mi away. Directions
- ORH Worcester Regional Airport, Worcester — 21 mi away. Directions
- BOS Boston Logan International Airport, Boston — 24 mi away (major hub). Directions
From Route 495: Take exit 21A (West). Follow through Hopkinton center where the road merges with Route 135. Ashland center is about 3.5 miles from the exit. From Route 9: Go south on Route 126 to Framingham center (about 2 miles). Turn west on Route 135. Ashland center is about 4 miles from Framingham center. The towns are also reachable by Route 16 for points east and west, and Route 126 for points north and south.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 1-day itinerary
Day 1
- Morning Ashland State Park, Hopkinton State Park
- Lunch Burnam's Supper House
- Afternoon Lake Winthrop, Slot Car Racing at Modelville Hobby
- Dinner Carbone's Restaurant
- Evening TJ Spirits
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Map
Every listing with a location. Tap a pin for its Google Maps link.
Get in
From Route 495: Take exit 21A (West). Follow through Hopkinton center where the road merges with Route 135. Ashland center is about 3.5 miles from the exit. From Route 9: Go south on Route 126 to Framingham center (about 2 miles). Turn west on Route 135. Ashland center is about 4 miles from Framingham center. The towns are also reachable by Route 16 for points east and west, and Route 126 for points north and south.
Get around
- MBTA Boston-Worcester Line , Ashland MBTA Station, Pleasant St.
- Metro-West Regional Transit Authority , Stops in Ashland along Route 126 and Route 135.
Do
Do Lake Winthrop
Tiny Lake Winthrop has several small unstaffed parks and remains open year round. Pleasure Point, just off Winthrop Street features a small beach and a boat launch onto the lake. Stoddard Park features a beach, a gazebo, playing fields and trails leading to Patoma Park.
Buy
Eat
- John Stone's Public House, 179 Main St., +1 508-881-1778, . was built in 1834 by John Stone to take advantage of the new railroad. The pub is reputed to be haunted .
Eat Oregon Club
Entrees $20, sides $5". Opened in 1922 as a prohibition era speak easy hosting several legendary local figures.
Eat Mexico City Taqueria
Family-owned restaurant serving authentic Mexican dishes, beer, wine and margaritas
Eat Erica’s Ristorante
Eclectic Italian. 82-seat dining room, and a bar area that can accommodate 60. There is also patio space and a private room that can hold 45.
Drink
Drink TJ Spirits
A Rural pub with lots of outdoor seating (smoking allowed). Caters to a very mixed local crowd.
Drink Ashland Ale House
Casual family restaurant and pub serving lunch and dinner. Live entertainment on Friday and Saturday nights.
Sleep
Go next
- Boston - 90 East. About 40-80 minutes away.
- Portsmouth NH - 495 North to 95 North. About 1 hour 15 minutes away.
- Cape Cod - 495 South. About 1-2 hours away.
Nearby
Framingham
City / town · 39 listings · 3 mi away
Natick
City / town · 27 listings · 6 mi away
Boroughs
City / town · 64 listings · 6 mi away
Marlborough
City / town · 9 listings · 7 mi away
Wayland
City / town · 11 listings · 9 mi away
Milford
City / town · 5 listings · 9 mi away
Wellesley
City / town · 24 listings · 9 mi away
Upton
City / town · 4 listings · 9 mi away
My experience
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