Twenty minutes by train from North Station, Lynn is a city with such a sordid historical reputation that it was known as the “City of Sin”.
The exact origin of the jingle, “Lynn, Lynn, City of Sin” is unknown, but it might have something to do with the city’s hardscrabble heritage.
Long a manufacturing powerhouse, Lynn’s was known for shoemaking, a trade that goes back to the earliest days of settlement here.
By the turn of the 20th century Lynn was the world-leader in shoe production, with 230+ factories kicking out more than a million pairs a day.
On the water there’s a string of public sandy beaches, which have a wild beauty at all times of year but are a magnet for visitors in the summer months.
In the mid-19th century the city became a favored escape for affluent Bostonians, and those sumptuous mansions remain between Lynn’s percolating downtown and the coast.
1. Lynn Shore Reservation
More than 20 acres of Lynn’s majestic coastline is open to the public, at King’s Beach, Red Rock Park and Lynn Beach.
The beaches are a wonderful attraction at any time of year, but are obviously at their best on those long summer days. Parking is rarely a problem, especially the large stretches of on-street spaces behind King’s Beach and Lynn Beach.
The coastline here is relatively sheltered, so the surf is usually calm or moderate. Low tide exposes an enormous expanse of hard-packed sand at King’s Beach, and you’ll be able to walk out far into Nahant Bay.
On the southwest side, the Lynn Shore Reservation merges with the Nahant Beach Reservation, continuing down the peninsula for a combined two miles of sandy beachfront.
2. Downtown Lynn
With arts, dining, shopping and elegant brick architecture Lynn has all the ingredients for a first-rate downtown area.
In 2021 a parcel of downtown Lynn was designated as Commonwealth’s inaugural cultural district, and Central Square can be the starting point for a great day out, combining food (20+ international eateries), public art, museums and shopping.
There’s a farmers’ market on Central Square, on Thursdays 11 am-3 pm, July through October.
Between downtown Lynn and the Atlantic Coast is the Diamond Historic District, with hundreds of magnificent mid-19th century residences, from the time when Lynn was a fashionable summer resort.
3. Lynn Museum and Historical Society
Right by Central Square, and an anchor for the cultural district is Lynn Museum and Historical Society, established in 1897.
The main permanent exhibit is Industry & Craft: People At Work In Lynn, chronicling the city’s various industries and livelihoods down the years, with a focus on shoemaking.
You’ll also get to know Elihu Thomson (1853-1937), the Lynn-based inventor and engineer whose Thomson-Houston Electric Company merged with the Edison General Electric Company in 1892 to become General Electric.
There are always interesting temporary shows, devoted to local art, Victorian furnishings, Black history and many other topics.
4. Lynn Woods
About one fifth of Lynn’s total area is taken up by this forested and rock-strewn park, which was officially established in the 1880s.
This land has been public since the 17th century, when it was used as a community woodlot. Spreading across the south side of Lynn Woods is Breed’s Pond, initially created for industrial use in the 1840s and then dammed to become a public water supply 30 years later.
The highest point in the city is the summit of Burrill Hill, and this is capped with Stone Tower, built for fire observation in the 1930s and now a wonderful lookout for Lynn and Boston to the southwest.
The park’s rugged terrain is streaked with trails, and is one of the best spots in the Boston area for mountain biking and bouldering.
5. Northern Strand Community Trail (Bike to the Sea Trail)
Opened in phases between 2013 and 2021, this 10-mile multi-use public path links several North Shore cities between the Mystic River in Boston and Lynn.
Much of the Northern Strand Community Trail is on the former route of the Saugus Branch Railroad of the Boston & Maine Railroad.
Close to Boston, this passes through newly revitalized communities like Everett and Malden, with several brewpubs by the trail in Everett, and a choice of restaurants in Malden with decks right on the trail.
In Saugus and Revere the route takes you next to restored patches of marshland for birdwatching. When we wrote this list, plans were afoot to extend the trail from Lynn down the peninsula to Nahant.
6. High Rock Tower Reservation
Lynn’s most emblematic landmark is the 85-foot tower and observatory crowning a hill with a wonderful panorama of the city and Atlantic coastline.
Built in 1904, High Rock Tower is a Romanesque Revival structure, one of 400 buildings designed for Lynn by architect Holman King Wheeler (1859-1943).
The encompassing park was laid out in 1907 by the Olmsted Brothers, while this vantage point has a history reaching back much further.
In the 1600s the summit is known to have been a gathering place for the Pawtucket Native Americans, as well as the headquarters of their chief, Nanapashemet.
In the mid-19th century, Jesse Hutchinson of the Hutchinson Family Singers, an abolitionist singing group, purchased the property from the Pawtucket tribe.
After settling here he constructed a wooden tower that would be the predecessor to the current structure, and donated the land to the city in 1853 for the construction of an observatory.
The tower and observatory—the latter rebuilt at the turn of the new millennium—are open to the public on select evenings in summer.
7. Lynn Memorial Auditorium
Marking the northwestern limit of downtown Lynn is a monumental Art Deco building constructed in the late 1940s.
The National Register of Historic Places since 2005, the complex houses the city’s main administrative offices, including the council chambers and mayor’s office.
But also here is a 2,000-seat auditorium that has hosted some world famous names like the Beach Boys, Fats Domino, Billy Preston and Roy Orbison.
The Lynn Memorial Auditorium had some fallow years beginning in the 1970s, but was brought back to life with a complete rehabilitation in 2002.
There’s a big helping of live music by top recording artists and tribute acts, as well as comedy shows, dance, magic shows and talks by prominent cultural figures.
8. Lynn Shore Promenade
One of the joys of Lynn’s extensive waterfront is its accessibility on foot or by bicycle. Set along the seawall, the paved promenade has fabulous views, especially if you come for the sunrise.
Behind King’s Beach this path is buffered from Lynn Shore Dr by a grassy bank, and departs the road altogether in Red Rock Park.
You’re never more than a minute or two from the nearest bench if you want to contemplate the scenery. In the north the promenade brings you to a clutch of ice cream parlors and restaurants in Swampscott.
Follow the trail south and you’ll travel down the Nahant peninsula next to Long Beach as far as Little Nahant Island.
9. Red Rock Park
The beachfront in the Lynn Shore Reservation is interrupted by a nub of land with exhilarating views.
Edged by the promenade that runs along the seawall, Red Rock Park has a large patch of grass and benches for those who want to bask in the beautiful vistas out into the Atlantic, south to Nahant and southwest to Boston.
Depending on the tide, there’s normally a web of little tide pools in the rocks at the tip of the headland, with interpretive signs on hand to help you identify some of the residents.
10. Saugus Iron Works National Historic Site
For industrial history of a much older kind, the site of the first integrated ironworks in North America is a few minutes away in Saugus.
This was established in 1646 by John Winthrop the Younger (1606-1676) and operated for the next quarter of a century. The buildings were soon lost to the underbrush, before preservation efforts began at the end of the 19th century.
The site became a national park in 1968 and has a reconstructed blast furnace, forge, shear, slitter rolling mill and a ¼-ton trip hammer, all powered by seven giant waterwheels.
This all stands next to a wharf where the iron was once loaded onto ocean-going vessels, as well as a restored house from the 1600s, thought to be the former home of the ironmaster.
11. Lynn Heritage State Park
Easily missed along the Lynnway and surrounded by new waterfront housing developments, there’s a small waterfront park on Lynn Harbor celebrating the city’s history, nature and coastline.
This is presented along a boardwalk, with nine panels composed of mosaics from ceramics and Venetian glass.
The park also shines as a place to enjoy the scenery, watching the water traffic in and out of the neighboring marina, backdropped by Boston’s skyline.
When we wrote this article plans were in motion to transform the neighboring harbor into a green waterfront neighborhood with even more public access via the Lynn Harborwalk.
12. Grand Army of the Republic Museum
Lynn has one of the country’s last functioning Grand Army of the Republic Halls, and the last to be found in Massachusetts.
This organization was founded by Union Army veterans in the wake of the Civil War, and the hall in Lynn was constructed in 1885.
This is maintained by a diverse team of history enthusiasts, and continues to honor those who fought to save the Union in the Civil War. Inside you can check out six rooms of memorabilia, from the Revolutionary War through WWI.
The standout is the main hall on the third floor, 56 x 46 feet, retaining its opulent original furnishings, with photograph portraits of veterans on almost every inch of wallspace.
13. Capitol Diner
Opposite the Lynn Museum downtown you’ll happen upon an exciting slice of history at this compact boxcar diner dating back to 1928.
This is thought to be the last surviving diner to have been designed by the J. G. Brill Company, which built rolling stock, trolleys, buses and diners up to the middle of the 20th century.
The Capitol Diner is three bays wide and ten long, with a lot of century-old features still intact inside.
This is a breakfast and lunch spot, closing at 2 pm and frequented for its omelettes, pancakes and other breakfast favorites like eggs benedict, chipped beef and French toast.
14. Pine Grove Cemetery
Perched on the hills next to Lynn Woods, Pine Grove Cemetery was established in 1849 and encompasses around 250 acres, about a third of which are developed. Many people come to this peaceful place for the greenery and views across to the Boston skyline.
In the 1930s the Works Progress Administration (WPA), constructed a fieldstone wall around the cemetery. This is spuriously claimed to be the second-longest wall of its kind in the world, after the Great Wall of China.
There are numerous famous interments at Pine Grove Cemetery, including Medal of Honor recipients, Baseball stars, entrepreneurs, U.S. Representatives and architect Holman K. Wheeler, who had made an enduring impression on the Lynn cityscape.
15. Nahant Beach Reservation
At the head of the Nahant peninsula, the Lynn Beach becomes Long Beach, with a 1.3-mile stretch of wide sandy shoreline continuing to the south.
Long Beach is open all year, but naturally becomes a major draw in the summer for sunbathing, swimming, launching boats and long walks by the Atlantic for people who want to feel the soft sand between their toes.
At the northern end, right on the boundary with Lynn, there’s a playground, accompanied by a visitor center at the James J. Ward Bath House, with ball fields and tennis and racquetball courts just across the road.