🌿 RelaxedLong weekend · from Boston, MA

Vineyards, Arboretums & Autumn Harvests

Savor hand-picked autumn flavors and golden landscapes while wandering through vineyard rows and arboretum pathways.

Day 1 — Greenvale VineyardsDay 2 — Connecticut College ArboretumDay 3 — Leyden Farm Vineyard & Winery

Day 1 — Greenvale Vineyards

🚗 2 hr 27 min driving📍 5 stops

🌅

Morning

🚗

Drive

Boston, MA → Greenvale Vineyards

1 hr 44 min

Greenvale Vineyards

★ Reviews →

Discover award-winning wines and rolling vineyard views in a peaceful Rhode Island setting perfect for a leisurely afternoon escape.

~1.5 hrs📍 See location

🍽️

Lunch

🍽️ Lunch~1 hr

White Horse Tavern

Established in Newport, RI in 1673 and still operating — the original beamed ceilings and Colonial-era character are intact. Colonial American food in one of the oldest dining rooms in the country.

★ Reviews →American Restaurant📍 Maps →

4 options · tap to switch

☀️

Afternoon

🚗

Drive

Greenvale Vineyards → Shepherd's Run

23 min

Shepherd's Run

★ Reviews →

Experience farm-to-table dining in a rustic countryside atmosphere that embodies the ultimate slow-food philosophy.

~1.5 hrs📍 See location

🌙

Evening

🚗

Drive

Shepherd's Run → Newport Vineyards

20 min

Newport Vineyards

★ Reviews →

Sip premium wines while overlooking Narragansett Bay, combining coastal relaxation with Rhode Island's thriving wine culture.

~1 hr📍 See location

🛏️

Castle Hill Inn

A Gilded Age estate overlooking Narragansett Bay on Newport's Ocean Drive — the Castle Hill Inn has been the benchmark Newport stay for a reason. The bluff-top lawn at sunset is exceptional, and the rooms in the main historic house are worth the premium over the beach cottages.

Day 2 — Connecticut College Arboretum

🚗 1 hr 58 min driving📍 5 stops

🌅

Morning

🚗

Drive

Greenvale Vineyards → Connecticut College Arboretum

1 hr 23 min

Connecticut College Arboretum

★ Reviews →

Wander through 750 acres of serene gardens and walking trails showcasing diverse plant collections in a tranquil natural sanctuary.

~1.5 hrs📍 See location

🍽️

Lunch

🍽️ Lunch~1 hr

Captain Scott's Lobster Dock

A no-frills lobster dock in New London, CT where whole lobsters and lobster rolls come off the boat and onto paper plates at outdoor picnic tables. Get there before the line builds.

★ Reviews →Seafood Restaurant📍 Maps →

3 options · tap to switch

☀️

Afternoon

🚗

Drive

Connecticut College Arboretum → The Spa at Norwich Inn

15 min

The Spa at Norwich Inn

★ Reviews →

Indulge in rejuvenating spa treatments and wellness experiences designed to melt away stress in an elegant, peaceful setting.

~1 hr📍 See location

🌙

Evening

🚗

Drive

The Spa at Norwich Inn → On The Waterfront Restaurant

20 min

🍽️ Dinner~1 hr

On The Waterfront Restaurant

Enjoy fresh seafood and scenic water views in a laid-back atmosphere perfect for unwinding with friends or family.

★ Reviews →Seafood Restaurant📍 Maps →

4 options · tap to switch

🛏️

Saybrook Point Resort & Marina - Luxury Connecticut Oceanside Hotel

A full-service marina resort at the mouth of the Connecticut River where it meets Long Island Sound — boat slips, a spa, and rooms that frame the tidal estuary. The most complete waterfront resort on the Connecticut shoreline.

Day 3 — Leyden Farm Vineyard & Winery

🚗 3 hr 41 min driving📍 4 stops

🌅

Morning

🚗

Drive

Connecticut College Arboretum → Leyden Farm Vineyard & Winery

50 min

Leyden Farm Vineyard & Winery

★ Reviews →

Explore a charming family-owned winery with tastings, beautiful grounds, and a genuine commitment to sustainable vineyard practices.

~1.5 hrs📍 See location

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Lunch

🍽️ Lunch~1 hr

The Middle of Nowhere Diner

A Vermont-style roadside diner that earns its name in the best way — home cooking, enormous portions, and the kind of place you mention when you get home.

★ Reviews →Diner📍 Maps →

4 options · tap to switch

☀️

Afternoon

🚗

Drive

Leyden Farm Vineyard & Winery → Saltwater Farm Vineyard

38 min

Saltwater Farm Vineyard

★ Reviews →

A coastal vineyard perched above Stonington harbor with tasting rooms set in a restored Connecticut barn — savor estate-grown chardonnay and rosé while watching sailboats drift across Fishers Island Sound below.

~1.5 hrs📍 See location

🌙

Evening

🚗

Drive

Saltwater Farm Vineyard → Cornerstone Pub

22 min

🍽️ Dinner~1 hr