Brookline, New Hampshire, is a small, characterful Hillsborough County town that sits just above the Massachusetts state line — a community of farms, stone walls, river corridors, and a village center whose compact Main Street and Meetinghouse Hill preserve the texture of 18th-century New England with remarkable completeness. Incorporated in 1798, Brookline built its early identity around the Nissitissit River watershed and the agriculture and modest industry that sustained its families through the 19th century. The town’s most tangible historical landmarks are clustered around Meetinghouse Hill Road, where a granite marker identifies the site of the 1791 meetinghouse that stood until it burned in 1915 — well positioned at the hilltop in the classic New England tradition of civic and spiritual visibility — and the Brookline Historical Society in a beautiful new barn addition with historical pieces on display preserves the documentary record of a community whose stability and continuity have been its most defining characteristics. The former Brookline Railroad Station on Route 13 is a perfectly maintained 19th-century train depot that is privately owned and not open to the public, but whose restored exterior — easy to appreciate with a slow drive past or a few minutes parked across the street — stands as a beautiful physical reminder of the Boston and Maine Railroad era that connected even the smallest southern New Hampshire towns to the wider world. Anchoring Brookline’s present-day cultural identity entirely is Averill House Vineyard on Averill Road — a beloved family estate winery open Friday through Sunday with vineyard table seating by reservation, a rotating selection of estate whites and reds including the acclaimed Cinematic red wine, charcuterie boards, yoga events, wine tours led by knowledgeable and personable staff, and a commitment to charitable giving tied to the property’s elephant imagery that makes tasting here feel like supporting something genuinely good in addition to drinking something genuinely delicious.
Brookline’s most singular outdoor attraction is one of the most extraordinary public spaces in all of southern New Hampshire. The Andres Institute of Art Sculpture Park on Route 13 — founded by retired mechanical engineer Paul Andres on Big Bear Mountain — is a free, donation-supported outdoor sculpture park with 12 miles of trails winding through beautiful forested terrain past more than 100 sculptures by international artists, with benches and picnic tables throughout, restrooms at the visitor center, trail maps at the entrance, an indoor exhibit space, live music and symposium events, and a summit marked by a large blue skatepark sculpture that rewards those who make the uphill climb with a sense of genuine accomplishment and artistic discovery — a parallel experience of art and nature that visitors describe as deserving three or four hours at minimum and return visits in every season. The Bartell Trailhead on Route 13 in northern Brookline provides a complementary woodland hiking experience with trails of varying difficulty through deep forest past old cellar holes, stone walls, mill foundations, a footbridge, logging clearings, and wetlands that make it a genuinely historical landscape in addition to a physical one. The Nissitissit River Trail and Potanipo Rail Trail — accessible from parking near the Andres Institute — add riverside and lake-view walking to Brookline’s outdoor portfolio, with beautiful water views across Potanipo Pond in all seasons and a quick 10-to-20-minute loop option for those with limited time.
Brookline’s dining scene is anchored by two outstanding Route 13 establishments that together cover every occasion from morning coffee to Saturday evening dinner. Brookline’s Finest at 106 Route 13 — located at the Andres Institute campus — is an irresistibly cozy café, bakery, takeout kitchen, and vendor shop open seven days a week, with gluten-free scones described as among the most delicious anywhere, fresh pies, cakes and fudge, everything bagels with cream cheese, morning coffee in a rustic atmosphere with quiet country music, locally made gift items, and take-home dinners that regulars rely on when they don’t want to cook — a place whose smell alone upon entry earns five-star reviews and whose friendly, welcoming staff make every visit feel like a neighborhood gathering. Chrysanthi’s Restaurant at 204 Route 13 is the town’s anchor full-service dining destination and one of the most enthusiastically reviewed Greek and Mediterranean restaurants in the region — a family-run gem that regulars have been visiting for nearly a decade, open Tuesday through Saturday, with outstanding fried clams, lobster rolls in summer, mezzo plates, Greek-inspired dishes made with locally sourced ingredients, excellent pizza, perfectly executed veal Parmesan, impeccable service from staff who are described by name and praised for patience and recommendations, fabulous cocktails including a standout pumpkin martini, and a warm dining room atmosphere with many regulars and a server who occasionally sings along to the background music in a way that reviewers describe as making the whole experience feel genuinely joyful. Together, these two establishments make Brookline’s Route 13 corridor one of the most rewarding small-town dining destinations in Hillsborough County.
