This well-heeled town in northeastern Massachusetts was incorporated as long ago as 1646, and has the highest point in Essex County, with views of the Boston skyline, 20 miles away.
Andover is known for the ultra-prestigious secondary school Phillips Academy, founded in 1778 and with Humphrey Bogart, George H. W. Bush, George W. Bush, Jack Lemmon, Frederick Law Olmsted and Bill Belichick in a big list of important alumni.
The Addison Gallery of American Art, boasting one of the world’s great collections of American painting, is on the campus and offers free admission.
Helping to preserve the town’s natural landscapes is the Andover Village Improvement Society (AVIS), dating back to 1894 and the second-oldest organization of its kind in the United States.
The AVIS manages almost 30 reservations in the town, with more than 30 miles of trails, including a long section of the Bay Circuit Trail.
1. Addison Gallery of American Art
Part of Phillips Academy, this museum has one of the world’s great collections of American art. The Addison Gallery was founded in 1931 and is set on the academy’s campus, with more than 17,000 works in its collection, from the 18th century to the present day.
There are pieces by a raft of luminaries, such as Georgia O’Keeffe, John Singleton Copley, Mary Cassatt, Alexander Calder, John Singer Sargent, James McNeill Whistler, Jackson Pollock, Winslow Homer, Edward Hopper and many more.
Typically, the museum puts on 12 exhibitions a year, with selections from that immense inventory and major traveling shows.
A community-oriented institution, the Addison Gallery offers free admission and is engaged in a range of educational programs for everyone from pre-kindergarten children to art educators.
2. Ward Reservation
On a landscape of rolling hills, including the highest points in Essex County, there’s more than 700 acres of public protected land to the southeast of downtown Andover. For centuries this was farmland, initially settled in the 1600s by Nicholas Holt.
His descendants remained here until the late 19th century, and in 1940 the land was donated to the Trustees of Reservations by the widow of Charles W. Ward in his memory.
The highest summit is the panoramic Holt Hill (more next), while there’s an equally satisfying view from Boston Hill, accessible via the Blue Loop. Also important is the Pine Hole Bog, a glacial kettle hole bog that you can cross on a 700-foot boardwalk.
3. Holt Hill
The biggest draw in the Ward Reservation is this 420-foot drumlin, marking the highest point in Essex County.
In a large clearing, Holt Hill is capped with the “Solstice Stones,” arranged like a compass to align with the sunset on the longest and shortest days of the year.
The view from the summit is staggering, rolling out some 20 miles to the Boston skyline. This has been a key vantage point for centuries, and in 1775 Andover’s townsfolk stood at this exact point to observe the burning of Charlestown in the Battle of Bunker Hill.
4. Bay Circuit Trail
This 200-mile greenway and rail bends through Boston’s outlying suburbs, from Newburyport in the north to Duxbury in the south.
Andover and North Andover are on more than 19 miles of the Bay Circuit Trail, as it traverses the towns in a northwesterly direction on its way to the bank of the Merrimack River.
One of the special things about the path here is that it connects a long chain of spaces that are managed by the Andover Village Improvement Society (seven in total, as well as Harold Parker State Forest).
So as you travel through these hills, woods, bogs and riverbanks you’ll see northeastern Massachusetts in its most natural state. The route is marked with plastic markers sporting the Bay Circuit logo
5. Downtown Andover
Andover has an upmarket central commercial district, designed for walking, littered with interesting architecture and brimming with eateries and interesting stores.
A mainstay is the august Andover Town Hall, built in the Romanesque Revival style in 1858, while the wedge-like Musgrove Block (1895) is a local icon.
Further south, at 97 Main Street, the Andover Historical Society is based at the Federal-style Amos Blanchard House, built 1818-19.
In the summer, Andover is just the place for dining alfresco, and there’s something for all palates whether you’re in the mood for Thai, pizza, Mexican, Italian, Greek, New England-style seafood, steak, Mediterranean…the list goes on.
On Saturdays in summer, you have to include the farmers’ market in your plans, and on Thursday evenings there’s a summer concert series on the Town Hall’s front plaza.
6. Harold Parker State Forest
A section of the Bay Circuit Trail crosses this 3,300-acre expanse of forest, overlapping with several neighboring towns and laced with more than 100 vernal pools.
Established in 1916, Harold Parker State Forest is an early example of reforestation by Massachusetts, and was the site of several improvement projects by the Civilian Conservation Corps (CCC) in the 1930s and 1940s.
The rolling landscape here was molded in the Ice Age by glacial activity, signs of which remain in the many glacial erratics strewn among the hardwood, hemlock and white pine forest.
The vast trail system at the forest includes 35 miles of logging roads open to the public, and mountain bikers can hit a network of single track trails that would take days to fully explore.
There’s a day-use area at Berry Pond, and the Lorraine Park Campground has 85 campsites, offering boating, swimming and fishing.
7. Moncrieff Cochran Bird Sanctuary
Open to the public, this 65-acre space is on Phillips Academy property, mixing rich nature with interesting history.
The ponds here were dammed in 1929-30 when the Olmsted Brothers were hired to design a bird sanctuary for the edification of the school’s students.
This featured plantings of rhododendron, azalea, wild blueberry and laurel, along with a massive collection of mostly waterfowl, all in a fenced site.
After a time the sanctuary was allowed to return to nature, but the vestigial clusters of rhododendron and laurel are in bloom in June and July.
There are miles of rolling trails across the property, and close to Rabbit Pond you’ll find a granite boulder with a marker from 1910, dedicated to the early Andover Theological Seminary students who established the American Society of Missions.
The seminary shared this land with Phillips Academy between 1807 and 1965.
8. Oak & Iron Brewing Company
There’s some striking old industrial architecture along the Shawsheen River in Andover, and one of the finest examples, at 18 Red Spring Road, houses the town’s local craft brewery, which opened in 2017.
Oak & Iron Brewing Company makes unique seasonal beers, often with ingredients from the region, as well as a wide selection of classics.
There’s a Golden Ale (Andover Easy Ale), Kölsch (Vorfreude), Dunkelweizen (Andover Runs on Dunkel), Oatmeal Stout (Ballardvale Black) and several hoppy Pale Ales (Rivah Bendah, Greenway, New England Project and more.
You’ve got a cozy patio, board games and a menu of beer-appropriate food, from Bavarian pretzels to a hot dog cooked in the brewery’s beer.
9. Pomps Pond
From mid-June to late August you can head to Pomps Pond, on Abbot Road for some fun in the sun.
Wrapped in woodland, this body of water was once the property of the formerly enslaved Pompey Lovejoy (1724-1826), remembered in Andover for making election cake and root beer for town meetings and funerals.
There’s a beach area here for swimming, sunbathing, volleyball and picnics. You’ve also got a concession stand, children’s playground and kayak, canoe and sailboat rentals.
There are trails along the water, and off season the beach is open to dog walkers. Pomps Pond makes up 16 acres of Andover’s 62-acre Recreation Park complex, with facilities including four tennis courts, lighted pickleball courts and a lighted ballfield.
10. Andover Farmers’ Market
There’s a flourishing farmers’ market in downtown Andover, held on Saturdays, 10 am to 1 pm from mid-June to mid-October.
This event has a beautiful setting at the Romanesque Revival South Church, completed in 1860 and the fourth meeting house on this site since 1709.
It’s not unusual to find more than 30 vendors at the market, selling local fruit, vegetables, herbs, maple syrup, cut flowers, plants, fresh roasted coffee, nuts oils, baked goods, spices, teas, sauces, seafood, wine and baked goods.
There’s often a choice of prepared food here, and a large contingent of craft vendors selling jewelry, essential oils, candles, organic cosmetics, scrubs, greeting cards and a lot more besides.
11. Sarkisian Farms Driving Range & Ice Cream
If you’re keen to improve your golf swing there’s an affordable driving range in Andover. This is on a farm established in the 1930s by one Ovagen Sarkisian, a recent immigrant who had fled the Armenian genocide.
The range has 35 lighted tees, multiple targets (30-250 yards), a sand trap and putting green, while lessons are available if you want some extra help with your game.
The driving range opened in 1994, and on its tenth anniversary an ice cream stand was added. This is a local summer staple serving award-winning Richardson’s Ice Cream made in Middleton, MA, as well as Richie’s Slush, and a range of custom sundaes, frappes and floats.
12. Stevens-Coolidge House & Gardens
Effortlessly close in North Andover is the elegant estate of Helen Stevens Coolidge and husband John Gardner Coolidge (1863-1936), who was briefly United States Minister to Nicaragua under Theodore Roosevelt.
John was also a descendant of Thomas Jefferson, and was the nephew of the famous collector and art patron Isabella Stewart Gardner.
The property had been in Helen’s family since 1729, and the couple oversaw a transformation of the estate, combining two late-Federal farmhouses into one Colonial Revival residence, and planting ornate formal gardens.
This is all now a museum run by the Trustees of Reservations, with collections of European decorative arts, American furniture and Asian art. There are public events all year round, and one highlight is the bloomfest in spring when some 175,000 bulbs are in flower.
13. Deer Jump Reservation
In the northwest of Andover, the Bay Circuit Trail intersects with another path tracing Andover’s Merrimack River frontage for almost its entirety.
Andover is relatively unique in that the majority of the riverbank is reserved for public recreation and conservation. So you have a path that runs from the line with Lawrence to Tewksbury in the west, crossing bluffs, passing boulders and running through lush hardwood forest composed of black, paper and silver birch, as well as beech, elm, maple and ash.
On the trail you’ll see Pine Island, the site of a village for the Pennacook Indians, controlling river traffic at a violent time in the 17th century.
14. Penguin Park
Once the lifeblood of local industry, the Shawsheen River winds through the town and flows into the Merrimack at North Andover.
There are long-term plans to build a greenway on the course of the river in Andover, and in the meantime you can access a number of public greenspaces on the riverbanks.
One of these is Penguin Park, a pastoral swath of open fields with a trail on the shore weaving through woods. This is a fantastic spot for a picnic in summer, and there’s a playground with equipment geared towards toddlers.
15. Andover Village Industrial District
You can also give yourself a little informal tour of the industry once powered by the Shawsheen River. This can be done at the Andover Village Industrial District, which includes the home of Oak & Iron Brewing.
With industrial and residential buildings (Federal and Greek Revival) dating back as much as 200 years, the district is mostly on Railroad St, Red Spring Rd, Shawsheen Rd, Essex St and Stevens St.
One imposing complex here is the Marland Mill, for spinning and carding, dating to 1885, but with accompanying buildings going back at least half a century earlier.
Today the factory is a senior living complex. Another mammoth factory building can be found at 30 Railroad St, where the Tyer Rubber Co, (a division of Converse Corp.), is now another apartment complex.