September 13, 2021

8 architectural experiences to feast your eyes on during Trails and Sails

by joeyphoenix

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Are you an architecture appreciator (who is fascinated by facades and bolstered by buttresses) ready to stretch your legs and crane your neck this fall north of Boston? Lucky for you, the annual Trails and Sails is hosting a series of architectural happenings with you in mind.

What is Trails and Sails?

Trails and Sails runs from Friday Sept. 17 through Sunday Sept. 26, 2021.

Entering into its 20th year, Trails & Sails is an event series that brings awareness and appreciation for heritage resources around the county. Historically, Trails & Sails has focused on outdoor activities such as guided hikes and excursions on the water but over the years the event series has grown to include tours of historic houses, lectures on Essex County history, and demonstrations for cultural activities. Learn more at

Explore Remond Family history at Hamilton Hall during the Hamilton Hall History Quiz and Open House

Where: Hamilton Hall, Salem, MA

When: Wednesday, September 22, 2021 @ 4:00 pm – 6:00 pm and Sunday, September 26, 2021 from 11:00 am – 1:00 pm.

On September 22nd and 26th, Explore Remond Family history at Hamilton Hall. The Remonds, who were free African-Americans, left a legacy of social activism and hospitality that we continue to celebrate today. Visitors can enjoy educational displays while hunting for the answers to a corresponding quiz. Your quest for answers will also give you a chance to tour the Hall. Built in 1805, Hamilton Hall is considered one of America’s finest examples of Federalist architecture.

Take a Walking Tour of Historic Downtown Marblehead

Where: 188 Washington St., Marblehead

When: Friday, September 24th and Saturday, September 25th, 2021 from 1:00 pm to 3:00 pm

A walk around the historic downtown area of Marblehead, highlighting its historic architecture and the town’s dramatic and often traumatic social history due to perils at sea, storms, fires, and the service of over 1,000 men & boys in 3 different wars within 100 years. Widespread poverty followed all of those — but that is what preserved the nearly 300 houses surviving from before 1775 (out of about 520 at that time), when Marblehead was one of the most populous metropolis in British North America.

Special Instructions: Tour begins outside main front entrance to Abbot Hall and covers less than 1/2 mile in the 2-hour timeframe (mostly walking or standing). Restrooms in basement level of Abbot Hall (stairs or elevator). Optimium parking is behind or beside Abbot Hall (not ON Washington St.). Pleasant St. before Rockaway St. is another option, just two blocks from the starting point.

Reservations: email or call 781-631-1762

Bonus: Pair this with the Tour & History of Fort Sewall ~ estab. 1644 for a full Marblehead experience.

Celebrate iconic buildings in Salem’s McIntire Historic District by going on an Architectural Treasure Hunt

Where: 9 Chestnut St, Salem, MA 01970

When: Daily during Trails and Sails

Celebrate iconic buildings in Salem’s McIntire Historic District by going on an Architectural Treasure Hunt! Use the answer bank to identify features of the following places: Hamilton Hall, Historic New England’s Phillips House, Pickering House and Salem Athenaeum. At each property, you will find a fact sheet challenging you to identify the building’s architectural details. The fact sheets are at the rear entrance of Phillips House, and at the front entrance of the other three properties. You can find the digital copies at the host websites.

Special Instructions: Bring your own pen.

Bella Building Tour

Where: Hilldale Cemetery Association | 2 Railroad Square, Haverhill, MA

When: Friday, September 17, 2021 from 11:30 am to 1:00 pm

Stroll through the streets of historic downtown Haverhill. Explore Haverhill’s rich Italian culture and architectural history. The walk will explore the part of the Italian district that includes River St, Washington St, and the lower part of Mt Washington Hill. Please wear comfortable shoes.

Historic Fletcher Steele Garden Tour

Where: Rolling Ridge Retreat and Conference Center | 660 Great Pond Rd, North Andover, MA 01845

When: Tuesday, September 21, 2021 from 10:00 am to 12:00 pm

Fletcher Steele is one of the most influential landscape architects of the early twentieth century. For 60 years he practiced landscape architecture as a fine art, designing nearly 700 gardens. The garden at Rolling Ridge was the first of his creations. Join us for a tour of this historic space of natural beauty on the shore of Lake Cochichewick. Although the fountain is not in operation and the grounds are being restored, you will discover the visionary genius of Steele.

Special Instructions: Please wear walking shoes. There is no charge for the morning garden tour. Lunch and afternoon art tour have a fee. Unfortunately, portions of the garden and mansion are not wheelchair accessible. Tour will start with gathering in the Tyson Meeting Room.

Self-guided Tours at Hammond Castle Museum

Where: Hammond Castle Museum | 80 Hesperus Ave, Gloucester, MA 01930

When: Wednesday, September 22, 2021 from 9:30 am to 4:00 pm

Take a self-guided tour of Hammond Castle Museum! Built by John Hays Hammond in the 1920’s as a home for his extensive collection of medieval artifacts and his research laboratory. The first 30 walk-in guests on Wednesday, September 22 will receive free admission for a self-guided tour of the Museum and the grounds. During your visit you can explore the expansive rooms, see the medieval architectural components and collections, and wander on the back lawn overlooking the ocean.

Manchester History and Architectural Walking Tour

Where: Manchester Historical Museum | 10 Union St, Manchester-by-the-Sea, MA 01944

Saturday, September 18, 2021 @ 10:00 am to 11:30 am

Enjoy a stroll through historic Manchester-by-the-Sea while looking at architectural styles & learn about the history of this sea side town. This guided walking tour takes about 90 minutes & covers the center of town, starting & ending at the Manchester Historical Museum which is located in the 1823 Federal mansion, the Trask House.

Special Instructions: This tour will keep within a 2 mile radius but will be 1 & 1/2 hrs of walking so wear comfortable shoes. Tour will start at 10am. Museum will be open afterwards.

Tiffany Windows of St. Stephens Memorial Church

Where: St. Stephens Memorial Church, Lynn | 74 S Common St, Lynn, MA 01902

When: Saturday, September 25, 2021 10:00 am to 2:00 pm

St. Stephen’s Memorial Church is an incredibly beautiful reddish granite building built in 1881 on Lynn Common. Enjoy a tour of the church and learn about the collection of over 41 Tiffany stained glass windows, perhaps the oldest ecclesiastical Tiffany windows in the world. Two very large windows were designed by the famous sculptor Augustus Saint-Gaudens. It is also the burial place of Lt. Col. Charles Redington Mudge, a Civil War hero who died at Gettysburg, July 3, 1863, and in whose memory the church was given by his father Enoch Redington Mudge.

Special Instructions: Masks will be required for all entering the church

Trails and Sails runs from Friday Sept. 17 through Sunday Sept. 26, 2021. Learn more at