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The Convent Guest House
The Convent Guest House - dream vacation

The Convent Guest House Main street LanesboroughLanesborough

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Lanesborough is a small town in the Berkshires of Massachusetts.

Get in

Lanesborough is just north of Pittsfield on Route 7 and Route 8. Coming from the north, it is south of New Ashford on Route 7 and southwest of Cheshire on Route 8. The town can also be entered from the west through Hancock along Brodie Mountain Road. The Hancock and New Ashford routes are quite scenic, with beautiful views of the Taconic Range.

Get around

By car

The main routes through Lanesborough are Route 7 and Route 8, which stretch parallel north-south all the way through Lanesborough. Rt. 7 and 8 are connected by the Berkshire Mall Road near the Pittsfield border and Pontoosuc Lake. Additionally, Summer St, turning into Old State Rd., will run through Berkshire Village into Rt. 8 near Cheshire. Swamp Rd. off Summer St. turns into Old State Rd. and also connects with Rt. 8, and Partridge Rd. off Summer St. runs into Pittsfield near the Allendale Plaza. From Hancock in the west, Rt. 7 is accessible from Brodie Mt. Rd., either directly near the New Ashford border or else from Brodie Mt. Rd. across Bailey Rd., which joins with Rt. 7 near the base of Mt. Greylock.

By bus

Lanesborough is served by several intercity bus lines offering regular service to Boston, New York, Albany, Hartford and points in between.


  • Mount Greylock State Reservation, West Mountain Rd. to Cheshire Harbor Trail (for hike). Run by the Massachusetts Department of Natural Resources, this 12,500-acre (50.6-km²) area features the state's only sub-alpine forest. About 70 miles (110 km) of trails traverse the mountain, including the Appalachian Trail. Five lean-to shelters are available for backpacking. The summit features Bascom Lodge which was built from local materials in the late 1930s and offers lodging and hot food. Also at the summit is Veterans War Memorial Tower, a 93-ft (28-m) tall Quincy granite tower with possible 90-mile views.
    • 1 Mt. Greylock State Reservation/Visitors' center, 30 Rockwell Road, ☏ +1 413-499-4262. Memorial Day to Labor Day: from 9AM-9PM; Labor Day to Columbus Day: 9AM-7PM; Winter hours, Columbus Day to Memorial Day: 9AM-4PM. Closed: Thanksgiving, Christmas and New Years Day.. Has park trail maps and orientation, regional tourist information. Exhibits focus on the natural and cultural history of the park. 
  • 2 Balance Rock State Park, Balance Rock Rd (Along Balance Rock Rd. No numbered street address, but the there is a sign marking the entrance. To get onto Balance Rock Rd.: From the north, take Bull Hill Rd. off Rt.7, turn onto Narragansett, and take a right from Narragansett onto Balance Rock. From the south, take Pecks Rd. in Pittsfield. It will turn into Balance Rock Rd.). A park in Pittsfield State Forest, featuring a large rock balanced on top of a smaller rock. Hiking, fishing, hunting, and snowmobiling. (updated Jun 2016)


  • 1 Ramblewild, 110 Brodie Mtn Road (on Brodie Mtn Road, near the Bailey Road junction), toll-free: +1-844-472-6253. Forest adventure park, with family and fitness activities available. Includes ropes courses and hiking and snowshoe trails. (updated Apr 2016)
  • 2 Donnybrook Country Club, 775 Williamstown Road (on Rt. 7, near the border with New Ashford), ☏ +1 413 499-7888. A golf course with scenic views of the Taconic Range. $20-$35. (updated Apr 2016)
  • 3 Pontoosuc Lake (there are many public entrances to Pontoosuc Lake, with access points on Rt. 7 and off Bull Hill Rd. in Lanesborough and Hancock Rd. in Pittsfield). Boating, fishing, swimming, and other water recreation. Boat rentals are available. 
  • 4 Baker's Golf Center, 658 South Main Street (on Rt. 7, adjacent to the Rt.7-Rt.8 connector road), ☏ +1 413 443-6102. 10AM-7:30PM, weather permitting. 6:30PM is the last time slot for mini-golf. Mini-golf course and driving range. Established in 1943. (updated Apr 2016)
  • 5 Skyline Country Club, 405 South Main Street (On Route 7, near the Rt. 7-Rt. 8 connector road), ☏ +1 413 445-5584. 8AM-8PM. Golf course with scenic views of Pontoosuc Lake and the Taconic Range $14-300. (updated Apr 2016)
  • 6 Ashuwillticook Rail Trail, Rt. 8. Old State Road (main entrance is at the Berkshire Mall Rd. junction with Rt. 8). A 10-foot wide, 11-mile paved rail trail path. The Ashuwillticook (ash-oo-will-ti-cook) Rail Trail runs parallel to Route 8 through the towns of Cheshire, Lanesborough and Adams. The southern end of the trail begins at the entrance to the Berkshire Mall off Route 8 in Lanesborough. The northern end is at Adams center. The trail passes Cheshire Reservoir, the Hoosic River, and several wetland habitats with abundant wildlife. Parking lots and restrooms are available along the way. A pamphlet with maps is widely available. Bicycles are welcome. 
  • 7 Bill Laston Memorial Fields, 417 North Main Street (along Route 7 / North Main Street). Public park and sports fields. Seecum Brook flows through the park and is available for wading and swimming. No dogs allowed. (updated Aug 2020)


  • 1 Lanesboro Junction, 1 North Main Street (at the junction of Route 7 / North Main Street with Summer Street), ☏ +1 (413) 997-4350. Local craft store (updated Aug 2020)
  • 2 Target, 655 Cheshire Road (take either Route 8 and turn onto Old State Road, or take the US 7 Rte 8 Connector Road), ☏ +1 413 236-4210. Located at the site of the Berkshire Mall. While the Mall has ceased operation, Target is still open. (updated Aug 2020)
  • 3 Dollar General, 525 S Main St (on Rt. 7, adjacent to the Post Office), ☏ +1 413 347-4046. 8AM-10PM. Various low priced groceries and accessories. (updated Apr 2016)


  • 1 Olde Forge Restaurant (Old Forge), 125 N Main St (On Rt. 7, next to the Mobil station), ☏ +1 413-442-6797. Su-Th noon-10PM, F Sa noon-11PM. One of the staple dining locations in Lanesborough, known for its tasty wings and fried food, salad bar, and assortment of beer. (updated Apr 2016)
  • 2 Bob's Country Kitchen, 42 S Main St (on Rt. 7 in downtown Lanesboro, near to St. Luke's and the Summer St. junction), ☏ +1 413 499-3934. 6:30AM-8PM. A staple Lanesborough dining location, known for its home-style meals. Breakfast is served all day. $11-30. (updated Apr 2016)
  • 3 Mad Jack's BBQ, 126 S Main Street (On Rt. 7), ☏ +1 413 442-2290. Thursday & Friday 4PM-9PM; Saturday noon - 9PM; closed Sunday - Wednesday. Bar and grill, also does catering. (updated May 2016)
  • 4 Matt Reilly's Pub (Matt Reilly's Irish Pub), 750 S Main St (on Rt. 7, on the shores of Pontoosuc Lake on the Lanesborough-Pittsfield border; near the Rt. 7-Rt. 8 connector road, across from the Gulf/BP station), ☏ +1 413 447-9780. 11AM-9PM. Staple dining location of Lanesborough. Features Irish cuisine, with a bar & grill. $11-$30. (updated Apr 2016)
  • 5 Lanesboro Restaurant & Pizza (Lanesboro Pizza House), 739 South Main St. (On Rt. 7, right on the Pittsfield border.), ☏ +1 413 442-0600. Su M 11AM-9PM, F Sa 11AM-10PM. Family owned and operated restaurant since 1996, specializing in pizza and Greek cuisine. The pizza is not recommended. Located near the shores of Pontoosuc Lake, with a view of the lake and the Taconic Range. (updated Apr 2016)
  • 6 Pasta's Arizona Pizza Co, 660 Cheshire Rd (on Rt. 8, near the Old State Rd junction and Berkshire Mall entrance; next to Brookhouse Sports Bar), ☏ +1 413 499-5562. Su-Th 11AM-10PM, F Sa 11AM-11PM. Moderately priced pizza, with appetizers and meals also served $11-30. (updated Apr 2016)
  • 7 Brookhouse Sports Pub & Restaurant, 650 Cheshire Rd (on Rt. 8, near the Old State Rd junction and Berkshire Mall entrance, next to Arizona Pizza), ☏ +1 413 499-3331. 11:30AM-close, closed on Mondays. Bar & grill. Reviews are mixed, especially toward the service. $11-30. (updated Apr 2016)


  • 1 Lanesboro Wines & Spirits, 162 S Main St (Directly along Rt. 7). On the former location of the Coyote Den, now Lanesboro Wines & Spirits. A wine shop, not primarily a bar. (updated Apr 2016)
  • 2 Pontoosuc Package Store, 731 S Main St (on Rt. 7, near the Pittsfield border along Ponoosuc Lake), ☏ +1 413 447-9556. M-Sa 11AM-11PM. A small package store with craft and brand name beer, along with wines and spirits. (updated May 2016)


  • 1 Lanesboro Country Inn, 499 South Main St., ☏ +1 413-442-1009. Cozy sleeping accommodations, located a minute's walk from Pontoosuc Lake. Reviews recommend the cabins over the motel lodgings. $70-100. (updated Apr 2016)
  • 2 The Weathervane Motel, 475 South Main St. (on Rt. 7, near the Bull Hill Rd junction), ☏ +1 413 443-3230. AAA approved, with special rates for AAA members. In-room phones, A/C, color cable TV, HBO, efficiency suite. Child and pet friendly. (updated Apr 2016)
  • 3 Old Stone School Cottage, 736 N Main St (take North Main St off Rt. 7), ☏ +1 413 442-0996. A quaint bed and breakfast. Built in 1832, it served as a schoolhouse until 1950. Lodgers will have the entire building to themselves. 2-bedroom cottage, can house four (plus accommodates 2 floor mattresses). $115; rates may vary, contact owner. (updated May 2016)
  • 4 Hidden Valley Campground, 15 Scott Rd. (15 Scott Rd. is the mailing address; the camp is on Scott Rd, off N. Main St.; to find the camp, look for the turn off near 705 N. Main St. and Wirtes Farm), ☏ +1 413-447-9419, toll-free: +1-877-392-2267. Campground with a view of the Taconic Range. Will take reservations. Rates are calculated for a family of 5 (2 adults and 3 children up to age 18). Various on campus activities are available. $34/night for tent sites and 30 Amp RVs, $39 for 50 Amp RVs. Special seasonal rates apply, and reduced rates for stays of 1 week or longer. (updated Apr 2016)
  • 5 Whippletree Bed and Breakfast, 10 Bailey Road (on the corner of Bailey Road and Route 7; if going northbound it will be on the right, southbound on the left; Bailey Road on that side of Route 7 is unpaved), ☏ +1 413 443-9874. Bed and Breakfast. (updated Aug 2020)
  • 6 Tuckered Turkey, 30 Cheshire Road (at the junction of Cheshire Road and Prospect Street; take either street to arrive at destination.), ☏ +1 413 442-0260. Bed & Breakfast. Has WiFi. No TV or phone. (updated Aug 2020)
  • 7 Sheeps Heaven View, 105 Brodie Mountain Road (take Brodie Mountain Road off Route 7 near the border of New Ashford if you are coming from the Lanesborough side; if coming from Hancock, take Brodie Mountain Road off of Route 43), ☏ +1 413 446-6559. Superhost on Airbnb. $129 a night. (updated Aug 2020)

Go next


The nearby city of Pittsfield (south on Route 7 and Route 8) is the hub of northern Berkshire County, with numerous restaurants, lodgings, and cultural attractions, including the Colonial Theater. The next town further south is Lenox, the home of Tanglewood, the Boston Symphony Orchestra's summer home.


Williamstown is about twenty minutes north on Route 7, and contains several cultural attractions, including the Clark Art Institute and the historic Williams College. From there, the state of Vermont is a short drive to the north, and North Adams a short drive to the east.


To the west of Lanesborough is Hancock, where Jiminy Peak, one of the prime ski resorts in the area, is located on Brodie Mountain Road.

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